3-(4-Phenylphenyl)prop-2-enoic acid → HCID 69208772、化合物

HRID 29692

反応式

HRID 29692 の反応式
[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

参加物

6

反応物 3

HCID 254923-(4-Phenylphenyl)prop-2-enoic acidHCID 516892Sodium BicarbonateHCID 57419527HCID 57419527、化合物

生成物 1

HCID 69208772HCID 69208772、化合物収率 79.2%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 24386Thionyl Chloride溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-fc4d352f78474d82a83dbd78f5fdcee5
出典データセット
uspto-grants-2008_09
特許番号
US07420083B2

関連ノート

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