Pyridine → HCID 18319605, compound

HRID 1699383Notes

Reaction equation

HRID 1699383 reaction equation
[NH2:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23].N1C=CC=CC=1>ClCCl.C(OCC)(=O)C>[Cl:18][CH2:19][CH2:20][CH2:21][C:22]([NH:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:23]

Participants

6

Reactant 3

HCID 1049PyridineHCID 783704-Chlorobutyryl chlorideHCID 18319514HCID 18319514, compound

Product 1

HCID 18319605HCID 18319605, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 9-amino-2,3-dihydro-1-benzoxepin-4-carboxylate (0.35 g), 4-chlorobutyryl chloride (0.202 ml) and pyridine (0.146 ml) in dichloromethane (3.5 ml) was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, and the solution was washed successively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of n-hexane and ethyl acetate (3:1) as an eluent to give colorless crystals of ethyl 9-(4-chlorobutyryl)amino-2,3-dihydro-1-benzoxepin-4-carboxylate (0.48 g).

Workup

  1. washthe solution was washed successively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of n-hexane and ethyl acetate (3:1) as an eluent

Sources & evidence

ORD record
ord-6765332fd61a4d9e9013f085d5173cbd
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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