Phenylacetyl chloride → HCID 67441299, compound

HRID 2045600Notes

Reaction equation

HRID 2045600 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](N(CC)C(C)C)(C)C.[C:32]1([CH2:38][C:39](Cl)=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(OCC)(=O)C>ClCCl>[CH3:23][O:21][C:20]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:39](=[O:40])[CH2:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:3]=1)[C:17]([CH3:18])([CH3:19])[CH2:16]2)=[O:22]

Participants

6

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 86658612HCID 86658612, compound

Product 1

HCID 67441299HCID 67441299, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (150 mg, 0.48 mmol) and N,N-diisopropylethylamine (0.16 mL, 0.97 mmol) in dichloromethane (10 mL) was added 2-phenylacetyl chloride (0.1 mL, 0.63 mmol) with ice cooling. The resultant mixture was kept 0° C. for 10 h. Thin layer chromatography (petroleum ether:ethyl acetate=3:1, Rf=0.4) showed the reaction was complete. Solvent was removed in vacuo and the residue was purified by Prep. Thin layer chromatography (petroleum ether:ethyl acetate=3:1) to afford 139 mg of methyl-3,3-dimethyl-2-(3-(2-phenylacetamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxy late as a off-white solid. Yield: 67.1%. MS (ES+APCI) M+1-CH3O=397.1.

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue was purified by Prep

Sources & evidence

ORD record
ord-3f48c838a85b451187702f7861e02639
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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