HCID 8760959, compound → HCID 66965669, compound

HRID 1514863Notes

Reaction equation

HRID 1514863 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:18]([O-])=O>CCOC(C)=O.[Pd]>[NH2:18][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:2]=1[NH2:1])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)=[O:7]

Participants

4

Reactant 1

HCID 8760959HCID 8760959, compound

Product 1

HCID 66965669HCID 66965669, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-amino-N-(3-chloro-phenyl)-3-nitrobenzamide (590 mg) in EtOAc (200 mL) was added 10% Pd/C (100 mg). The reaction mixture was stirred overnight under H+ balloon. The reaction mixture was filtered through a Celite pad, washed with EtOAc. The solution was concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=20:80 to 100:0) to give of 3,4-diamino-N-(3-chloro-phenyl)-benzamide as a white solid: MS (m/z) 262 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 9.84 (s, 1H), 7.95 (t, 1H), 7.67 (d, 1H), 7.32 (t, 1H), 7.12 (m, 2H), 7.07 (dd, 1H), 6.54 (d, 1H), 5.12 (s, 2H), 4.63 (s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. washwashed with EtOAc
  3. concentrationThe solution was concentrated under reduced pressure
  4. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexane=20:80 to 100:0)

Sources & evidence

ORD record
ord-5cd6cb2e2daf496ebbd8a5e2c87c292b
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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