Thionyl Chloride → HCID 19967107, compound

HRID 2081602Notes

Reaction equation

HRID 2081602 reaction equation
O[CH:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)[CH3:3].S(Cl)([Cl:17])=O>O1CCCC1>[ClH:17].[Cl:17][CH:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8][CH2:7]2)[CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14373258HCID 14373258, compound

Product 1

HCID 19967107HCID 19967107, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 2 parts of intermediate 21, namely 3,4-dihydro-6-(1-hydroxyethyl)-2(1H)-quinolinone in 8.9parts of tetrahydrofuran were added 1.62 parts of thionyl chloride. Stirring at room temperature was continued overnight. The reaction mixture was evaporated and the residue was co-evaporated with methylbenzene, yielding 2.3 parts (93.4%) of 6-(1-chloroethyl)-3,4-dihydro-2(1H)-quinolinone hydrochloride (interm. 36).

Workup

  1. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-c6a44605115b4e9795d3ea3e5c82df7e
Source dataset
uspto-grants-1993_02
Patent number
US05185346

Reaction notes

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