GB456534A - Process for the manufacture of nitrogenous aromatic aldehydes - Google Patents
Process for the manufacture of nitrogenous aromatic aldehydesInfo
- Publication number
- GB456534A GB456534A GB1391035A GB1391035A GB456534A GB 456534 A GB456534 A GB 456534A GB 1391035 A GB1391035 A GB 1391035A GB 1391035 A GB1391035 A GB 1391035A GB 456534 A GB456534 A GB 456534A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aminobenzaldehyde
- hydroxyethyl
- chlorethyl
- methyl
- methylformanilide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
N-Halogenalkyl aromatic aminoaldehydes are prepared by treating N-halogenalkyl arylamines with formyl compounds of secondary amines in the presence of a halide or oxyhalide of sulphur or phosphorus. The N-halogenalkyl arylamines may be formed in situ from the corresponding N-hydroxyalkyl arylamines. The products may be treated to replace the halogen by another substituent, e.g. a hydroxy, alkoxy, sulphonic, amino or substituted amino group. Specified amines for use as starting materials are N-hydroxyethyl, N-hydroxypropyl and N-hydroxybutyl arylamines or their derivatives further substituted on the nitrogen atom, e.g. N-hydroxyethyl-N-methylaniline, N-hydroxyethyl - N - propylaniline, N - hydroxyethyl - N - butylaniline, N - hydroxyethyl - N - benzylaniline, N - di(hydroxyethyl)aniline, N - b -hydroxypropyl - N - methylaniline, N - hydroxyethyl-N-ethyl-m-toluidine, N-hydroxyethyl-N-butyl-m-chloraniline, N-hydroxyethyldiphenylamine, N - hydroxypropyl - N - butylaniline, and N-hydroxybutyl-N-ethylaniline. Specified formyl compounds are N-methylformanilide and N-formyldiphenylamine. Specified halides are phosphorus chlorides, phosphorus oxychloride and oxybromide, thionyl chloride, and sulphuryl chloride. In the examples: (1) N - chlorethyl - N - methyl - p - aminobenzaldehyde is obtained from N-hydroxyethyl-N-methylaniline, N-methylformanilide, and phosphorus oxychloride; N - chlorethyl - N - butyl - p - aminobenzaldehyde is similarly obtainable from N-hydroxyethyl-N-butylaniline; (2) N-di(chlorethyl)-p-aminobenzaldehyde is prepared from N - di(hydroxyethyl)aniline, N - methylformanilide, and phosphorus oxychloride; (3) N - chlorethyl - N - phenyl - p - aminobenzaldehyde is prepared from N-hydroxyethyldiphenylamine, N-methylformanilide, and phosphorus oxychloride; (4) N-chlorethyl-N-butyl-p-amino-o-chlorobenzaldehyde is prepared from N-hydroxyethyl - N - butyl - m - chloraniline, N-methylformanilide, and phosphorus oxychloride; (5) N-chlorethyl-N-methyl-p-aminobenzaldehyde is treated with aqueous or aqueous alcoholic soda solution to yield N-hydroxyethylN - methyl - p - aminobenzaldehyde; (6) N - di-(chlorethyl) - p - aminobenzaldehyde, treated as in example 5, yields p-morpholinobenzaldehyde; (7) N - chlorethyl - N - methyl - p - aminobenzaldehyde is heated with sodium sulphite solution to yield N - sulphoethyl - N - methyl - p - aminobenzaldehyde; N - sulphoethyl - N - benzyl - p - aminobenzaldehyde is similarly obtainable; (8) N-di-(chlorethyl)-p-aminobenzaldehyde, treated as in example 7, yields N-di(sulphoethyl)-p-aminobenzaldehyde; (9) N-di(chlorethyl)-p-aminobenzaldehyde is prepared from N-di(chlorethyl)-aniline, N-methylformanilide, and phosphorus oxychloride; (10) N-b -chloropropyl-N-methyl-p-aminobenzaldehyde is prepared from N-b -hydroxypropyl - N - methylaniline, N - methylformanilide, and phosphorus oxychloride; (11) N - chlorethyl - N - ethyl - p - amino - o - methylbenzaldehyde is prepared from N-hydroxyethyl-N-ethyl-m-toluidine, N-methylformanilide, and phosphorus oxychloride; (12) N-bromethyl-N-methyl-p-aminobenzaldehyde is prepared from N - hydroxyethyl - N - methylaniline, N - methylformanilide, phosphorus oxybromide, and phosphorus oxychloride; the product is then converted into N-methoxyethyl-N-methyl-p-aminobenzaldehyde by reaction with a solution of sodium in methyl alcohol; (13) N-bromethyl-N-methyl-p-aminobenzaldehyde is heated with diethylamine to yield N-diethylaminoethyl-N-methyl-p-aminobenzaldehyde; N-aminoethyl-N - methyl - p - aminobenzaldehyde is similarly obtainable. Specification 311,208, [Class 2 (iii)], is referred to. A sample has been furnished under Sect. 2 (5), of N-chlorethyl-N-ethyl-1-amino-4-naphthaldehyde, prepared from N-hydroxyethyl-N-ethyl-1-naphthylamine, N-methylformanilide, and phosphorus oxychloride.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1391035A GB456534A (en) | 1935-05-11 | 1935-05-11 | Process for the manufacture of nitrogenous aromatic aldehydes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1391035A GB456534A (en) | 1935-05-11 | 1935-05-11 | Process for the manufacture of nitrogenous aromatic aldehydes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB456534A true GB456534A (en) | 1936-11-11 |
Family
ID=10031599
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1391035A Expired GB456534A (en) | 1935-05-11 | 1935-05-11 | Process for the manufacture of nitrogenous aromatic aldehydes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB456534A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2437370A (en) * | 1945-03-09 | 1948-03-09 | Du Pont | Para-tertiary amino phenyl aldehydes |
US2573606A (en) * | 1946-12-02 | 1951-10-30 | Parke Davis & Co | Lower alkyl and alkenyl n-(1-naphthyl methyl) n-hydroxyethyl amines |
EP0331983A2 (en) * | 1988-02-24 | 1989-09-13 | F. Hoffmann-La Roche Ag | Stilbene derivatives, their preparation and their use in medicines |
US5250562A (en) * | 1988-02-24 | 1993-10-05 | Hoffmann-La Roche Inc. | Stilbene derivatives |
-
1935
- 1935-05-11 GB GB1391035A patent/GB456534A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2437370A (en) * | 1945-03-09 | 1948-03-09 | Du Pont | Para-tertiary amino phenyl aldehydes |
US2573606A (en) * | 1946-12-02 | 1951-10-30 | Parke Davis & Co | Lower alkyl and alkenyl n-(1-naphthyl methyl) n-hydroxyethyl amines |
EP0331983A2 (en) * | 1988-02-24 | 1989-09-13 | F. Hoffmann-La Roche Ag | Stilbene derivatives, their preparation and their use in medicines |
JPH023629A (en) * | 1988-02-24 | 1990-01-09 | F Hoffmann La Roche Ag | Novel stilbene derivative |
EP0331983A3 (en) * | 1988-02-24 | 1990-11-07 | F. Hoffmann-La Roche Ag | Stilbene derivatives, their preparation and their use in medicines |
US5106981A (en) * | 1988-02-24 | 1992-04-21 | Hoffmann-La Roche Inc. | Stilbene derivatives |
US5250562A (en) * | 1988-02-24 | 1993-10-05 | Hoffmann-La Roche Inc. | Stilbene derivatives |
US5378705A (en) * | 1988-02-24 | 1995-01-03 | Hoffmann-La Roche Inc. | Stilbene derivatives |
JP2556577B2 (en) | 1988-02-24 | 1996-11-20 | エフ・ホフマン―ラ ロシユ アーゲー | Novel stilbene derivative |
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