Lithium Hydroxide → HCID 21506098, compound

HRID 1287723Notes

Reaction equation

HRID 1287723 reaction equation
[NH:1]([C:8]1[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[N+:21]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[OH-].[Li+].[H][H]>O.[Pd]>[NH2:21][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([S:17](=[O:20])(=[O:19])[NH2:18])[C:8]=1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 14798Sodium HydroxideHCID 215060714-Anilino-3-nitro-5-sulphamyl-benzoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21506098HCID 21506098, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A suspension of 4-anilino-3-nitro-5-sulphamyl-benzoic acid (7 g) in water (80 ml) was adjusted to a pH of 9 by the addition of 2N sodium hydroxide or lithium hydroxide, and the resulting solution was hydrogenated at room temperature and 1.1 atmospheres hydrogen pressure after the addition of a palladium-on-carbon catalyst (0.3 g catalyst containing 10% Pd). After the hydrogen uptake had become negligible, the catalyst was removed by filtration, and the 3-amino-4-anilino-5-sulphamyl-benzoic acid was precipitated from the filtrate by addition of 4N hydrochloric acid until the pH was 2.5. After recrystallization from aqueous ethanol and drying in vacuo, the melting point was 251° C.

Workup

  1. customwas hydrogenated at room temperature
  2. customthe catalyst was removed by filtration
  3. customthe 3-amino-4-anilino-5-sulphamyl-benzoic acid was precipitated from the filtrate by addition of 4N hydrochloric acid until the pH was 2.5
  4. customAfter recrystallization from aqueous ethanol
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-38ab48e4a05a43a2b1765fc905ad37b9
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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