Ethyl 4-chloroacetoacetate → HCID 15462635, compound

HRID 1003210Notes

Reaction equation

HRID 1003210 reaction equation
[NH2:1][C:2]1[S:19][C:5]2[CH2:6][N:7]([C:10](=[O:18])[C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH2:8][CH2:9][C:4]=2[C:3]=1[C:20](=O)[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1.[Cl:32][CH2:33][C:34](=O)[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37].Cl.C(O)C>C(O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([N:7]2[CH2:8][CH2:9][C:4]3[C:3]4[C:2]([S:19][C:5]=3[CH2:6]2)=[N:1][C:34]([CH2:33][Cl:32])=[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:20]=4[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)=[O:18])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 69484Ethyl 4-chloroacetoacetateHCID 21887872Ethanol hydrochlorideHCID 22452748HCID 22452748, compound

Product 1

HCID 15462635HCID 15462635, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-6-(4-chlorobenzoyl)-3-(3,4-dimethoxybenzoyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (20.55 g), ethyl 4-chloroacetoacetate (8.17 g), hydrochloric acid-ethanol (23%, 7.34 g) and ethanol (80 ml) was stirred under refluxing conditions for 2.5 hours. The separating crystal was collected by filtration and recrystallized from ethyl acetate to yield ethyl 7-(4-chlorobenzoyl)-2-chloromethyl-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below) (12.38 g, 47%) as a light-yellow crystal having a melting point of 132 to 133° C. ##STR32##

Workup

  1. filtrationThe separating crystal was collected by filtration
  2. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-59681dae436e4c878e246805e0fefbf8
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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