3-(4-Phenylphenyl)prop-2-enoic acid → 2-{[(2E)-3-(1,1'-biphenyl-4-yl)prop-2-enoyl]amino}-4-hydroxybenzoic acid methyl ester

HRID 29692

Reaction equation

HRID 29692 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]([OH:11])=O)=[CH:3][CH:2]=1.[CH3:18][O:19][C:20](=[O:41])[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[NH:28]C(C1C2C(=CC=CC=2)C=CC=1)=O.C([O-])(O)=O.[Na+]>O=S(Cl)Cl.CC(C)=O>[CH3:18][O:19][C:20](=[O:41])[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[NH:28][C:9](=[O:11])/[CH:8]=[CH:7]/[C:4]1[CH:3]=[CH:2][C:1]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 254923-(4-Phenylphenyl)prop-2-enoic acidHCID 516892Sodium BicarbonateHCID 57419527HCID 57419527, compound

Product 1

HCID 692087722-{[(2E)-3-(1,1'-biphenyl-4-yl)prop-2-enoyl]amino}-4-hydroxybenzoic acid methyl esterYield 79.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A mixture of 3-biphenyl-4-yl-acrylic acid (0.449 g, 2.004 mmol) in SOCl2 (5 ml) was refluxed for 2 h. After cooling, the solvent was removed. The residue was dissolved in acetone and added into a stirred solution of 4-hydroxy-2-(naphthoylamino)-benzoic acid methyl ester (0.335 g, 2.004 mmol) in acetone (10 ml) with NaHCO3 (0.202 g, 2.405 mmol). After 18 h, the reaction mixture was concentrated. The residue was triturated with water, filtered and the solids rinsed with ether and dried to give 2-{[(2E)-3-(1,1′-biphenyl-4-yl)prop-2-enoyl]amino}-4-hydroxybenzoic acid methyl ester (0.593 g, 1.588 mmol, 79%) as an off-white solid, mp 292-296° C. 1H NMR (DMSO-d6) δ 3.88 (s, 3H), 6.57 (dd, 1H), 6.95 (d, 1H), 7.37-7.54 (m, 3H), 7.67 (d, 1H), 7.70-7.80 (m, 4H), 7.80-7.90 (m, 3H), 8.20 (dd, 1H), 10.55 (s, 1H), 11.20 (s, 1H); mass spectrum [ES(−)], m/z 372 (M−H)−.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperatureAfter cooling
  3. customthe solvent was removed
  4. dissolutionThe residue was dissolved in acetone
  5. concentrationthe reaction mixture was concentrated
  6. customThe residue was triturated with water
  7. filtrationfiltered
  8. washthe solids rinsed with ether
  9. customdried

Sources & evidence

ORD record
ord-fc4d352f78474d82a83dbd78f5fdcee5
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Linked notes

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