(1,1'-Biphenyl)-3-carboxylic acid → HCID 67214315, compound

HRID 2421608Notes

Reaction equation

HRID 2421608 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1>>[CH3:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH:22][C:10]([C:9]2[CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:15]=[CH:14][CH:13]=2)=[O:12])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 660354-Methylbenzylamine

Product 1

HCID 67214315HCID 67214315, compound

Procedure

Using preparation method 1, 3-phenylbenzoic acid (125 mg, 0.63 mmol) was reacted with 4-methylbenzylamine (96 mg, 0.7 mmol). The product was purified by flash chromatography on SiO2 using CH2Cl2/hexanes 50:50 then CH2Cl2 100%. White crystals were obtained (115 mg, 58%). NMR 1H (ppm, CDCl3): 7.99 (s, 1H), 7.73-7.69 (m, 2H), 7.58 (dd, J3=7.0 Hz, J4=1.4 Hz, 2H), 7.48 (t, J3=7.8 Hz, 1H), 7.43 (t, J3=7.6 Hz, 2H), 7.35 (tt, J3=7.2 Hz, J4=2.4 Hz, 1H), 7.29 (d, J3=8.6 Hz, 2H), 6.88 (d, J3=8.7 Hz, 2H), 6.36 (br. s, 1H), 4.59 (d, J3=5.5 Hz, 2H), 3.79 (s, 3H).

Workup

  1. customThe product was purified by flash chromatography on SiO2
  2. customWhite crystals were obtained (115 mg, 58%)

Sources & evidence

ORD record
ord-43b652a706264778a877c4bb855f9a86
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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