Diethyl Ether → HCID 86740156, compound

HRID 1248452Notes

Reaction equation

HRID 1248452 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[NH:17]([C:19]1[S:20][CH:21]=[CH:22][N:23]=1)[NH2:18].C(OCC)C>CO>[ClH:1].[S:20]1[CH:21]=[CH:22][N:23]=[C:19]1[NH:17][NH:18][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 268963Ethyl 4-Chloroquinoline-3-carboxylateHCID 119590662-Hydrazinylthiazole

Product 1

HCID 86740156HCID 86740156, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.63 g of ethyl 4-chloroquinoline-3-carboxylate and 0.80 g of 2-hydrazinothiazole in 22 ml of methanol is stirred for 26 hours at 23°; 22 ml of diethyl ether is added to the resulting slurry, which is then filtered. The precipitate is washed once with methanol-ether (1:1) and once with ether to yield ethyl 4-(2-thiazolylhydrazino)-quinoline-3-carboxylate hydrochloride as a yellow solid which is used directly in the above cyclization.

Workup

  1. filtrationis then filtered
  2. washThe precipitate is washed once with methanol-ether (1:1) and once with ether

Sources & evidence

ORD record
ord-c51a3308301b4bee96e89f6439df0e94
Source dataset
uspto-grants-1985_06
Patent number
US04524146

Reaction notes

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