HCID 54321252, compound → 3,4-Diamino-N-phenylbenzamide

HRID 1406434Notes

Reaction equation

HRID 1406434 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[N+:19]([O-])=O)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8])([O-])=O.[H][H]>C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[NH2:19])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8]

Participants

5

Reactant 2

HCID 54321252HCID 54321252, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 181854863,4-Diamino-N-phenylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product obtained at (1a) (19.0 g, 46.3 mmol) in 200 mL of THF was combined with 10% palladium on charcoal (3.0 g) and hydrogenated in a Parr apparatus at ambient temperature for 20 h at 3.5 bar hydrogen pressure. Then the mixture is filtered and the filtrate is concentrated i.vac. The residue is purified by chromatography on silica gel (eluent gradient: dichloromethane/(methanol/conc. ammonia=95:5)=100:0->92:8).

Workup

  1. additionA mixture of the product
  2. filtrationThen the mixture is filtered
  3. concentrationthe filtrate is concentrated i.vac
  4. customThe residue is purified by chromatography on silica gel (eluent gradient: dichloromethane/(methanol/conc. ammonia=95:5)=100:0->92:8)

Sources & evidence

ORD record
ord-2628b98d87ea48b0bf80e4ed9d5488e0
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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