Ethyl chloroformate → 3H-Azepino(4,5-b)quinoline-3-carboxylic acid, 1,2,4,5-tetrahydro-11-methyl-, ethyl ester

HRID 1288114Notes

Reaction equation

HRID 1288114 reaction equation
C([N:8]1[CH2:22][CH2:21][C:20]2[C:11](=[N:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19]=2[CH3:23])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(Cl)Cl>[CH2:28]([O:27][C:25]([N:8]1[CH2:22][CH2:21][C:20]2[C:11](=[N:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19]=2[CH3:23])[CH2:10][CH2:9]1)=[O:26])[CH3:29]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 21503431HCID 21503431, compound

Product 1

HCID 30440083H-Azepino(4,5-b)quinoline-3-carboxylic acid, 1,2,4,5-tetrahydro-11-methyl-, ethyl esterYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 gm (1.7 millimols) of 3-benzyl-1,2,4,5-tetrahydro-11-methyl-3H-azepino[4,5-b]quinoline were reacted in 5 ml of methylene chloride with a stoichiometric quantity (0.15 ml) of ethyl chloroformate for four hours at room temperature. After distilling off the methylene chloride and recrystallizing the residue from ether, the product was obtained with a yield of 52% of theory; m.p. 125° C.

Workup

  1. distillationAfter distilling off the methylene chloride
  2. customrecrystallizing the residue from ether
  3. customthe product was obtained with a yield of 52% of theory

Sources & evidence

ORD record
ord-58563429c8d94431ba10c8f84d0ee8b1
Source dataset
uspto-grants-1976_10
Patent number
US03987047

Reaction notes

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