Benzenepropanoic acid → HCID 67442300, compound

HRID 1801343Notes

Reaction equation

HRID 1801343 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O-:22])=[O:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[C:23]1([CH2:29][CH2:30][C:31]([OH:33])=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:34](N(CC)C(C)C)(C)C.P(Cl)(Cl)(Cl)=O>ClCCl>[CH3:19][C:17]1([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:34])=[O:21])[CH:14]=2)[NH:9][CH:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:31](=[O:33])[CH2:30][CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 86658612HCID 86658612, compound

Product 1

HCID 67442300HCID 67442300, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold mixture of 2-(3-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (150 mg, 0.48 mmol), 3-phenylpropanoic acid (95 mg, 0.73 mmol), N,N-diisopropyl ethylamine (0.20 mL, 1.16 mmol) in dichloromethane (10 mL) was added a solution of phosphorus oxychloride (0.06 mL, 0.63 mmol). Then the reaction mixture was stirred at room temperature overnight. LC-MS indicated that the starting material was consumed completely. Solvent was removed in vacuo and the residue was purified by Prep. Thin layer chromatography (petroleum ether/ethyl acetate=2:1) to afford 220 mg of methyl 3,3-dimethyl-2-(3-(3-phenylpropanamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylate as a pale yellow solid; Yield: 90%.

Workup

  1. customwas consumed completely
  2. customSolvent was removed in vacuo
  3. customthe residue was purified by Prep

Sources & evidence

ORD record
ord-e8e16af2014d47858e3a6cc7fc049c46
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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