Triethylamine → HCID 19898220, compound

HRID 1196408Notes

Reaction equation

HRID 1196408 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14])([O-:10])=[O:9].[C:20]1([CH:26]2[NH:31][C:30](=[O:32])[CH2:29][C:28](=O)[CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([C:28]1[CH2:27][CH:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:31][C:30](=[O:32])[CH:29]=1)=[O:14])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 111714746-Phenylazaperhydroine-2,4-dione

Product 1

HCID 19898220HCID 19898220, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (3.4 ml) was added at 0°-5° C. to a stirred solution of 2-nitrobenzoyl chloride (4.9 g) and 6-phenylpiperidine-2,4-dione (5 g) in dry dichloromethane (100 ml) and the mixture stirred at ambient temperature for 3.5 hours. The solution was washed successively with 2N hydrochloric acid (25 ml), water (2×25 ml), 5% w/v aqueous sodium carbonate solution (25 ml) and water (3×25 ), dried over magnesium sulphate and evaporated under reduced pressure to give a pale yellow solid which was recrystallised from a mixture of ethyl acetate and hexane (4:1; 20 ml) to give 5,6-dihydro-4-(2-nitrobenzoyl)-6-phenylpyridin-2(1H)-one (4.8 g), mp 139°-141° C., as a light yellow crystalline solid.

Workup

  1. washThe solution was washed successively with 2N hydrochloric acid (25 ml), water (2×25 ml), 5%
  2. dry with materialdried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. customto give a pale yellow solid which
  5. customwas recrystallised from a mixture of ethyl acetate and hexane (4:1; 20 ml)

Sources & evidence

ORD record
ord-b9b819ae03a54473b73b9f8d3659d4f5
Source dataset
uspto-grants-1992_05
Patent number
US05114461

Reaction notes

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