Cyclopropanecarboxylic acid → HCID 67442007, compound

HRID 1801301Notes

Reaction equation

HRID 1801301 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.[CH:23]1([C:26]([OH:28])=O)[CH2:25][CH2:24]1.[CH:29](N(CC)C(C)C)(C)C.P(Cl)(Cl)(Cl)=O>ClCCl>[CH:23]1([C:26]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]3[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:29])=[O:21])[CH:14]=4)[NH:9]3)[CH:5]=[CH:6][CH:7]=2)=[O:28])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 86658612HCID 86658612, compound

Product 1

HCID 67442007HCID 67442007, compoundYield 60%

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), cyclopropanecarboxylic acid (86.1 mg, 0.73 mmol), N,N-diisopropyl ethylamine (0.16 mL, 0.96 mmol) in dichloromethane (10 mL) was added a solution of phosphorus oxychloride (0.08 mL, 0.82 mmol). Then the reaction mixture was stirred at room temperature for 2.5 h. 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 109 mg of methyl 2-(3-(cyclopropanecarboxamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a pale yellow solid; Yield: 59.8%;

Workup

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

Sources & evidence

ORD record
ord-39d2405f7e6644fc931db3bf75b4c42b
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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