Acetyl chloride → HCID 67441301, compound

HRID 2045612Notes

Reaction equation

HRID 2045612 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](Cl)(=[O:34])[CH3:33].C(OCC)(=O)C>ClCCl>[C:32]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 86658612HCID 86658612, compound

Product 1

HCID 67441301HCID 67441301, compoundYield 76.3%

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 acetyl chloride (0.04 mL, 0.58 mmol) with ice cooling. The resultant mixture was kept 0° C. overnight. 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 129 mg of methyl 2-(3-acetamidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate as a off-white solid. Yield: 71.1%.

Workup

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

Sources & evidence

ORD record
ord-512f1fb36d26406087e7b0340a1b2fe0
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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