Hydrochloric Acid → HCID 12900700, compound

HRID 2166569Notes

Reaction equation

HRID 2166569 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[CH2:10]([N:17]1[CH2:22][C:21](OC)=[CH:20][C:19](=[O:25])[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>CCOCC.C1COCC1>[CH2:10]([N:17]1[CH2:22][C:21]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:20][C:19](=[O:25])[CH2:18]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 129006931-Benzyl-5-methoxy-1,2,3,6-tetrahydropyridin-3-oneHCID 178478127HCID 178478127, compound

Product 1

HCID 12900700HCID 12900700, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of m-chlorophenyl magnesium bromide (85 mM) in ether (50 ml) was treated dropwise with a solution of 1-benzyl-1,6-dihydro-5-methoxy-3-[2H]pyridone (16.3 g, 75 mM) in THF (75 ml) and stirred 1 hour. The reaction mixture was poured onto cold 2 N hydrochloric acid (150 ml) and stirred 30 min. Removal of the resulting precipitate by filtration, followed by air-drying and recrystallisation from ethanol gave the title compound as the hydrochloride hydrate (14.7 g) m.p. 143°-5°.

Workup

  1. stirringstirred 30 min
  2. customRemoval of the resulting precipitate
  3. filtrationby filtration
  4. customby air-drying
  5. customrecrystallisation from ethanol

Sources & evidence

ORD record
ord-c878901775d946a88597c2ee1935db5b
Source dataset
uspto-grants-1983_06
Patent number
US04387230

Reaction notes

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