Ethyl chloroformate → HCID 68140643, compound

HRID 1288130Notes

Reaction equation

HRID 1288130 reaction equation
OC1C=CC2N=C3CCNCCC3=C(C)C=2C=1.[Cl:18]C(OCC)=O.[CH2:24]([O:26][C:27]([N:29]1[CH2:43][CH2:42][C:41]2[C:32](=[N:33][C:34]3[CH:35]=[CH:36][C:37]([O:45]C(OCC)=O)=[CH:38][C:39]=3[C:40]=2[CH3:44])[CH2:31][CH2:30]1)=[O:28])[CH3:25].[OH-].[K+]>>[ClH:18].[CH2:24]([O:26][C:27]([N:29]1[CH2:43][CH2:42][C:41]2[C:32](=[N:33][C:34]3[CH:35]=[CH:36][C:37]([OH:45])=[CH:38][C:39]=3[C:40]=2[CH3:44])[CH2:31][CH2:30]1)=[O:28])[CH3:25]

Participants

5

Reactant 4

HCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 21503457HCID 21503457, compoundHCID 54416263HCID 54416263, compound

Product 1

HCID 68140643HCID 68140643, compoundYield 16%

Procedure

9-Hydroxy-1,2,4,5-tetrahydro-11-methyl-3-azepino[4,5-b]quinoline-carboxylic acid ethyl ester hydrochloride was prepared from 9-hydroxy-1,2,4,5-tetrahydro-11-methyl-3H-azepino[4,5-b]quinoline and ethyl chloroformate analogous to Example 63, followed by hydrolysis of the intermediate 9-(ethoxy-carbonyloxy)-1,2,4,5-tetrahydro-11-methyl-3-azepino[4,5-b]quinoline-carboxylic acid ethyl ester with dilute potassium hydroxide at 30° C.

Sources & evidence

ORD record
ord-23f52f61032f4b6e85e38083c6c5643f
Source dataset
uspto-grants-1976_10
Patent number
US03987047

Reaction notes

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