Lithium Hydroxide → 3-Amino-5-sulphamyl-4-(beta,beta,beta-trifluoroethoxy)-benzoic acid

HRID 1287756Notes

Reaction equation

HRID 1287756 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:19](=[O:22])(=[O:21])[NH2:20])[C:12]=1[O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:7]([OH:9])=[O:8])([O-])=O.[OH-].[Li+].[H][H]>O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([S:19](=[O:21])(=[O:22])[NH2:20])[C:12]=1[O:13][CH2:14][C:15]([F:17])([F:16])[F:18])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 215059913-Nitro-5-sulphamyl-4-(beta,beta,beta-trifluoroethoxy)-benzoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 215060013-Amino-5-sulphamyl-4-(beta,beta,beta-trifluoroethoxy)-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Nitro-5-sulphamyl-4-(β,β,β-trifluoroethoxy)-benzoic acid (2g) in water (30 ml) was adjusted to a pH of 9 by addition of lithium hydroxide, and the resulting solution was hydrogenated at room temperature and at a hydrogen pressure of 1.1 atmospheres after addition of Pd-on-carbon catalyst (0.2 g catalyst containing 10% Pd). After the hydrogen uptake had become negligible, the catalyst was removed by filtration, and the 3-amino-5-sulphamyl-4-(β,β,β-trifluoroethoxy)-benzoic acid was precipitated from the filtrate by addition of 4N hydrochloric acid until a pH of 2.5. After recrystallization from aqueous ethanol and drying, the melting point of the compound was 253°-254° C.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe 3-amino-5-sulphamyl-4-(β,β,β-trifluoroethoxy)-benzoic acid was precipitated from the filtrate by addition of 4N hydrochloric acid until a pH of 2.5
  3. customAfter recrystallization from aqueous ethanol
  4. customdrying
  5. customwas 253°-254° C.

Sources & evidence

ORD record
ord-5899a7f8a1304c598d4059a1dabd966e
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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