Methanol → HCID 58425607, compound

HRID 1966477Notes

Reaction equation

HRID 1966477 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=2)=[CH:6][C:5]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O-])=O.CO>>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=2)=[CH:6][C:5]=1[NH:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 46199380HCID 46199380, compound

Product 1

HCID 58425607HCID 58425607, compound

Procedure

To stirred solution 4′-nitro-3′-(phenylamino) biphenyl-3-carboxylic acid (0.5 g, 1.5 mmol) in methanol (5 mL) PtO2.H2O (30 mg, 0.0149 mmol) was added. The resulting mixture was stirred under H2 atmosphere at room temperature for 10 h. After completion of reaction (by TLC) it was filtered through celite, evaporated under vacuum to get the crude product. Flash chromatography gave 4′-amino-3′-(phenylamino) biphenyl-3-carboxylic acid which was isolated finally as dihydrochloride salt (0.4 g) 88% yield. 1H NMR (500 MHz, DMSO): δ 6.87 (t, J=7 Hz, 1H), 7.02 (d, J=6.5 Hz, 2H), 7.32 (m, 4H), 7.59 (m, 2H), 7.84 (d, J=7.8 Hz 1H), 7.91 (d, J=7.5 Hz, 1H), 8.09 (s, 1H). HRMS (ESI) calculated for C19H17N2O2: 305.1285, Found: 305.1279.

Workup

  1. additionwas added
  2. customAfter completion of reaction (by TLC) it
  3. filtrationwas filtered through celite
  4. customevaporated under vacuum
  5. customto get the crude product

Sources & evidence

ORD record
ord-9b90ed630d3c4054901c6b93d0726667
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

Loading…