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Triethylamine → 3-(3-methyl-isoxazol-5-yl)-4-phenyl-6-vinyl-1H-quinolin-2-one

HRID 2053426
Notes
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Reaction equation

HRID 2053426 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([CH:16]=[CH2:17])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[CH3:18][C:19]1[CH:23]=[C:22]([CH2:24][C:25](Cl)=[O:26])[O:21][N:20]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:18][C:19]1[CH:23]=[C:22]([C:24]2[C:25](=[O:26])[NH:1][C:2]3[C:3]([C:4]=2[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:12][C:13]([CH:16]=[CH2:17])=[CH:14][CH:15]=3)[O:21][N:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123668732-(3-Methylisoxazol-5-yl)acetyl chlorideHCID 59655024HCID 59655024, compound

Product 1

HCID 1360186653-(3-methyl-isoxazol-5-yl)-4-phenyl-6-vinyl-1H-quinolin-2-oneYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-amino-5-vinylbenzophenone (c) (0.1 g, 0.45 mmol), (3-methyl-isoxazol-5-yl)-acetyl chloride (0.9 mmol) [from example 4], triethylamine (0.20 mL) and DCM (10 mL) was heated to reflux overnight. After the mixture was cooled to room temperature and concentrated, the residue was purified by flash chromatography on silica gel (5% methanol in DCM) to give 3-(3-methyl-isoxazol-5-yl)-4-phenyl-6-vinyl-1H-quinolin-2-one (d) (0.12 g, 81%). 1H NMR (300 MHz, CDCl3) 8 12.68 (s, 1H), 7.74-7.65 (m, 1H), 7.52-7.41 (m, 4H), 7.30-7.13 (m, 3H), 6.58 (dd, J=11, 19.6 Hz, 1H), 6.45 (s, 1H), 5.62 (d, J=19.6 Hz, 1H), 5.18 (d, J=11 Hz,1H), 2.27 (s, 3H). MS: 329.2 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. customthe residue was purified by flash chromatography on silica gel (5% methanol in DCM)

Sources & evidence

ORD record
ord-4a93bf50938949cb8345beb414ae6a30
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07326788B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes