HCID 57962249, compound → tert-Butyl (3-{[(3-aminophenyl)acetyl]amino}phenyl)carbamate

HRID 541835Notes

Reaction equation

HRID 541835 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:18][CH:19]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH:17]=[CH:18][CH:19]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 57962249HCID 57962249, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57962170tert-Butyl (3-{[(3-aminophenyl)acetyl]amino}phenyl)carbamateYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (3-{[(3-nitrophenyl)acetyl]amino}phenyl)carbamate (0.35 g, 0.94 mmol) in methanol (100 mL) was added 10% palladium on carbon (1:10, Palladium:carbon black, 0.15 g, 0.13 mmol). The reaction was shaken under 60 psi hydrogen gas overnight. The crude mixture was filtered through celite and concentrated under vacuum to give the desired product (0.30 g, 94%). LCMS for C19H23N3O3 (M-tBu+H)+: m/z=286.0.

Workup

  1. filtrationThe crude mixture was filtered through celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-270278be8ca946d49928fcfffd8b94e5
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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