Methyl propiolate → HCID 11024936, compound

HRID 648533Notes

Reaction equation

HRID 648533 reaction equation
[OH-].[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N+:9]3[C:15]([OH:16])=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)S[C:10]=32)=[CH:5][CH:4]=1.[C:23]([O:27][CH3:28])(=[O:26])[C:24]#[CH:25]>C1(C)C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][N:9]3[C:10](=[C:24]([C:23]([O:27][CH3:28])=[O:26])[CH:25]=[C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:15]3=[O:16])[C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 13536Methyl propiolateHCID 21614600HCID 21614600, compound

Product 1

HCID 11024936HCID 11024936, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(ba) 4.2 g of 9-chloro-2-phenyl-5,6-dihydro-3-hydroxythiazolo[2,3-a]isoquinolinium hydroxide (internal salt) were heated under reflux for 4 hours in 100 ml of toluene together with 1.32 ml of methyl propiolate. After concentration in vacuo, the residue was chromatographed on silica gel with toluene/acetone (9:1). There was obtained methyl 10-chloro-6,7-dihydro-4-oxo-3-phenyl-4H-benzo[a]quinolizine-1-carboxylate of m.p. 139°-141° (from ethyl acetate).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was chromatographed on silica gel with toluene/acetone (9:1)

Sources & evidence

ORD record
ord-b49264748101433996ee7cd5e58a6df3
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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