Thionyl Chloride → HCID 54025343, compound

HRID 1288166Notes

Reaction equation

HRID 1288166 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:18]2[C:9](=[N:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]=2[CH3:21])[CH:8](O)[CH2:7]1)=[O:5])[CH3:2].S(Cl)([Cl:25])=O>>[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:18]2[C:9](=[N:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]=2[CH3:21])[CH:8]([Cl:25])[CH2:7]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 53875304HCID 53875304, compound

Product 1

HCID 54025343HCID 54025343, compound

Procedure

1 gm (3.3 millimols) of 5-hydroxy-1,2,4,5-tetrahydro-11methyl-3-azepino[4,5-b]quinoline-carboxylic acid ethyl ester was stirred for 2 hours with 20 ml of thionyl chloride at room temperature. The excess thionyl chloride was then distilled off in vacuo, the residue was dissolved in chloroform, the solution was dried with sodium sulfate, and the solvent was distilled off. After purification of the residue on a silicagel column with benzene/ethyl acetate (8:2) as the eluant, the yield was 0.55 gm (52% of theory), m.p. 131° C.

Workup

  1. distillationThe excess thionyl chloride was then distilled off in vacuo
  2. dissolutionthe residue was dissolved in chloroform
  3. dry with materialthe solution was dried with sodium sulfate
  4. distillationthe solvent was distilled off
  5. customAfter purification of the residue on a silicagel column with benzene/ethyl acetate (8:2) as the eluant

Sources & evidence

ORD record
ord-9adbbbdbf2a241d3aad2826b7091c370
Source dataset
uspto-grants-1976_10
Patent number
US03987047

Reaction notes

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