3-(4-Phenylphenyl)prop-2-enoic acid → HCID 69208772, 화합물

HRID 29692

반응식

HRID 29692 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 69208772HCID 69208772, 화합물수율 79.2%

시약·촉매·용매 2

HCID 180Acetone용매HCID 24386Thionyl Chloride용매

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-fc4d352f78474d82a83dbd78f5fdcee5
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420083B2

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