Hydrazine hydrate (1:1) → 2-chloro-N-[1-(2-hydrazino-2-oxoethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247527Notes

Reaction equation

HRID 1247527 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[S:31][C:8]2[NH:9][C:10]([C:12]([NH:14][CH:15]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([CH2:25][C:26]([O:28]C)=O)[C:16]3=[O:30])=[O:13])=[CH:11][C:7]=2[CH:6]=1>CCO>[Cl:4][C:5]1[S:31][C:8]2[NH:9][C:10]([C:12]([NH:14][CH:15]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([CH2:25][C:26]([NH:2][NH2:3])=[O:28])[C:16]3=[O:30])=[O:13])=[CH:11][C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 100020612-Chloro-N-[1-(methoxycarbonylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 587218262-chloro-N-[1-(2-hydrazino-2-oxoethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamideYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (1 mL, 20.6 mmol) was added to a suspension of methyl[3-{[(2-chloro-6H-thieno[2,3-b]pyrrol-5-yl)carbonyl]amino}-2-oxo-3,4-dihydroquinolin-1(2H)-yl]acetate (Example 1); 221 mg, 0.53 mmol) in EtOH (10 mL) and heated to reflux for 20 hours. On cooling the mixture was concentrated under reduced pressure and H2O (20 mL) added and the white precipitate filtered off and dried in vacuo to give the title product (169 mg, 76%) as an off white solid.

Workup

  1. temperatureto reflux for 20 hours
  2. temperatureOn cooling the mixture
  3. concentrationwas concentrated under reduced pressure and H2O (20 mL)
  4. additionadded
  5. filtrationthe white precipitate filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-841669d0fee34c89a61dc9fa036de4b9
Source dataset
uspto-grants-2006_10
Patent number
US07129249B2

Reaction notes

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