GB373085A - Manufacture of amino-substituted organic arsenic compounds - Google Patents
Manufacture of amino-substituted organic arsenic compoundsInfo
- Publication number
- GB373085A GB373085A GB812/32A GB81232A GB373085A GB 373085 A GB373085 A GB 373085A GB 812/32 A GB812/32 A GB 812/32A GB 81232 A GB81232 A GB 81232A GB 373085 A GB373085 A GB 373085A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- amino
- nitro
- arsonic
- methoxybenzene
- 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
- 125000003277 amino group Chemical group 0.000 title abstract 4
- 150000001495 arsenic compounds Chemical class 0.000 title 1
- 229940093920 gynecological arsenic compound Drugs 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 abstract 3
- HLVKIGYSNYOGBP-UHFFFAOYSA-N (2-amino-3-hydroxy-4-methoxyphenyl)arsonic acid Chemical compound NC1=C(C=CC(=C1O)OC)[As](O)(=O)O HLVKIGYSNYOGBP-UHFFFAOYSA-N 0.000 abstract 2
- JRIGVWDKYXCHMG-UHFFFAOYSA-N (5-arsoroso-2-hydroxyphenyl)azanium;chloride Chemical compound Cl.NC1=CC([As]=O)=CC=C1O JRIGVWDKYXCHMG-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 2
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical class O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 abstract 2
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229950008475 oxophenarsine Drugs 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- UHMSJNALTSEXGF-UHFFFAOYSA-N (1-hydroxy-6-methoxycyclohexa-2,4-dien-1-yl)arsonic acid Chemical class OC1(C(C=CC=C1)OC)[As](O)(=O)O UHMSJNALTSEXGF-UHFFFAOYSA-N 0.000 abstract 1
- DTXIANZDJZQKLS-UHFFFAOYSA-N (3-acetamido-4-methoxyphenyl)arsonic acid Chemical compound COC1=CC=C([As](O)(O)=O)C=C1NC(C)=O DTXIANZDJZQKLS-UHFFFAOYSA-N 0.000 abstract 1
- YARCNKWAIFQJDP-UHFFFAOYSA-N (3-amino-4-hydroxy-5-methoxyphenyl)arsonic acid Chemical compound COC1=C(O)C(N)=CC(=C1)[As](O)(O)=O YARCNKWAIFQJDP-UHFFFAOYSA-N 0.000 abstract 1
- MRJWAMKLXZNGOJ-UHFFFAOYSA-N (3-hydroxy-4-methoxy-2-nitrophenyl)arsonic acid Chemical compound COC1=C(O)C(=C(C=C1)[As](O)(O)=O)[N+]([O-])=O MRJWAMKLXZNGOJ-UHFFFAOYSA-N 0.000 abstract 1
- RUFOHZDEBFYQSV-UHFFFAOYSA-N 4-methoxy-3-nitroaniline Chemical compound COC1=CC=C(N)C=C1[N+]([O-])=O RUFOHZDEBFYQSV-UHFFFAOYSA-N 0.000 abstract 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N Arsenious Acid Chemical compound O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 abstract 1
- FGOFNVXHDGQVBG-UHFFFAOYSA-N N-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(C)=O FGOFNVXHDGQVBG-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- -1 arsenobenzenes Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- DQWRNQKJPNUTPJ-UHFFFAOYSA-N n-(2-methoxy-4-nitrophenyl)acetamide Chemical compound COC1=CC([N+]([O-])=O)=CC=C1NC(C)=O DQWRNQKJPNUTPJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- GPSSQIRGCXEBSH-UHFFFAOYSA-N oxoarsenic Chemical class [As]=O GPSSQIRGCXEBSH-UHFFFAOYSA-N 0.000 abstract 1
- AWYSLGMLVOSVIS-UHFFFAOYSA-N phenyl(phenylarsanylidene)arsane Chemical compound C1=CC=CC=C1[As]=[As]C1=CC=CC=C1 AWYSLGMLVOSVIS-UHFFFAOYSA-N 0.000 abstract 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Arsonic acids, arsenobenzenes, arsenoxides, and arsines.--Nitro-substituted 1-hydroxy-2-methoxybenzene-arsonic acids are reduced to the corresponding amino-substituted acids which may then be further reduced to the arsenoxide, arsenobenzene and arsine stages. The products possess therapeutic properties. According to the examples (1) 5-nitro-2-acetylaminoanisole is heated with caustic soda to replace the acetylamino group by hydroxyl, the product reduced, the amino group replaced by the arsonic acid residue, the product nitrated and finally treated with sodium hydrosulphite to reduce the nitro to the amino group; the resulting 3-amino-4-hydroxy-5-methoxybenzene-1-arsonic acid is then reduced to the arseno compound by means of hydrosulphite, or to the arsenoxide using sulphurous acid in the presence of hydriodic acid, or to the arsine with zinc and hydrochloric acid; (2) 2-amino-3-hydroxy-4-methoxybenzene-1-arsonic acid is prepared by diazotizing and arseniating 1-methoxy-2-nitro-4-aminobenzene, reducing to the amino-acid with hydrosulphite, acetylating, nitrating, replacing the acetylamino group with hydroxyl by heating with caustic soda, and finally reducing the nitro group of the resulting 2-nitro-3-hydroxy-4-methoxybenzene-1 - arsonic acid; (3) 1-methoxy-2-acetylaminobenzene is nitrated, reduced, diazotized, and treated with arsenious acid, the 3-acetylamino-4-methoxybenzene-1-arsonic acid formed then nitrated and the 2-nitro product worked up to the 2-amino-3-hydroxy-4-methoxybenzene-1-arsonic acid by the method indicated in (2) above.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE373085X | 1931-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB373085A true GB373085A (en) | 1932-05-19 |
Family
ID=6335979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB812/32A Expired GB373085A (en) | 1931-01-10 | 1932-01-11 | Manufacture of amino-substituted organic arsenic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB373085A (en) |
-
1932
- 1932-01-11 GB GB812/32A patent/GB373085A/en not_active Expired
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