HCID 10593901, compound → HCID 54127070, compound

HRID 744131Notes

Reaction equation

HRID 744131 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][C:13](=[O:24])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)[CH:3]=1.[H][H]>C(OCC)(=O)C.[Pt]=O>[NH2:21][C:17]1[CH:16]=[C:15]([CH2:14][C:13]([NH:12][C:4]2[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])=[O:24])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 10593901HCID 10593901, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54127070HCID 54127070, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of platinum oxide (0.35 g) in ethyl acetate (100 ml) containing methyl 4-chloro-2-(3-nitrophenyl)acetamidobenzoate (9.96 g, 28.6 mmol) was shaken under an atmosphere of hydrogen at 40 psi until hydrogen uptake had ceased. The suspension was filtered and the filtrate evaporated to leave methyl 2-(3-aminophenyl)acetamido-4-chlorobenzoate as a pale green solid (9.22 g); δ (CDCl3) 3.65 (2H, s, CH2), 3.66 (3H, s, OCH3), 6.61 (1H, dd, J 7.9 and 2.1 Hz, ArH), 6.70 (1H, s, ArH), 6.74 (1H, d, J 7.6 Hz, ArH), 7.01(1H, dd, J 8.6 and 2.0 Hz, 5-H), 7.14(1H, d, J 7.7 Hz, ArH), 7.89(1H, d, J 8.6 Hz, 6-H), 8.81 (1H, d, J 2.0 Hz, 3-H) and 11.03 (1H, br s, CONH).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-1a81441438a442e298ed82e606d50529
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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