Ammonium Chloride → N-(3,4-diaminophenyl)methanesulfonamide

HRID 717320Notes

Reaction equation

HRID 717320 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:13]([O-])=O.[BH4-].[Na+].[NH4+].[Cl-]>CO.CCOC(C)=O.[Pd]>[NH2:13][C:3]1[CH:4]=[C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 1270965376345-45-4

Product 1

HCID 12709656N-(3,4-diaminophenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

N-(4-amino-3-nitrophenyl)methanesulfonamide (1.5 g, 6.5 mmol) was dissolved in MeOH/EtOAc(1:1, 160 mL). To the above solution were slowly added 10% Pd/C (110 mg) and NaBH4 (418 mg, 11.0 mmol). The reaction mixture was stirred for 1 h, after which TLC showed absence of starting material. After addition of NH4Cl (400 mg), the reaction mixture was filtered through CELITE. The filtrate was concentrated and the product was used without further purification.

Workup

  1. filtrationthe reaction mixture was filtered through CELITE
  2. concentrationThe filtrate was concentrated
  3. customthe product was used without further purification

Sources & evidence

ORD record
ord-3684ccedc0ff439f945a34825669fedc
Source dataset
uspto-grants-2015_11
Patent number
US09193717B2

Reaction notes

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