HCID 21506083, compound → HCID 21505987, compound

HRID 918635Notes

Reaction equation

HRID 918635 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:15]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[N+:20]([O-])=O.[H][H]>[OH-].[Na+].[Pd]>[NH2:20][C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([S:16](=[O:19])(=[O:18])[NH2:17])[C:7]=1[NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:23])[CH3:1])[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 21506083HCID 21506083, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21505987HCID 21505987, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14798Sodium HydroxideSolvent

Procedure

4-(3-Dimethylaminopropylamino)-3-nitro-5-sulphamyl-benzoic acid (6.92 g) was dissolved in 2N sodium hydroxide (25 ml), and the solution was hydrogenated at room temperature and 1.1 atmospheres hydrogen pressure after the addition of a palladium-on-carbon catalyst (0.35 g catalyst containing 10% Pd.). After the hydrogen uptake had become negligible, the catalyst was removed by filtration, and the filtrate was adjusted to a pH of 8 by addition of 4N hydrochloric acid. The precipitated 3-amino-4-(3-dimethylaminopropylamino)-5-sulphamyl-benzoic acid was collected by suction and recrystallized from water. After drying in vacuo at 115°C for 2 hours, the melting point was 264°C (decomp.).

Workup

  1. customwas hydrogenated at room temperature
  2. customthe catalyst was removed by filtration
  3. additionthe filtrate was adjusted to a pH of 8 by addition of 4N hydrochloric acid
  4. customThe precipitated 3-amino-4-(3-dimethylaminopropylamino)-5-sulphamyl-benzoic acid was collected by suction
  5. customrecrystallized from water
  6. customAfter drying in vacuo at 115°C for 2 hours

Sources & evidence

ORD record
ord-750d2e7452f642c1acd4d00a84f1af30
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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