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Methanimidic acid, N-cyano-, ethyl ester → N-cyano-N'-(7-chloro-2-methylimidazo[2,1-a]isoquinolin-3-yl)formamidine

HRID 649157
Notes
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Reaction equation

HRID 649157 reaction equation
[C:1]([N:3]=[CH:4]OCC)#[N:2].[NH2:8][C:9]1[N:13]2[CH:14]=[CH:15][C:16]3[C:21]([C:12]2=[N:11][C:10]=1[CH2:23]C)=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22]>C(O)C>[C:1]([NH:3][CH:4]=[N:8][C:9]1[N:13]2[CH:14]=[CH:15][C:16]3[C:21]([C:12]2=[N:11][C:10]=1[CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 9920370Methanimidic acid, N-cyano-, ethyl esterHCID 201424443-Amino-7-chloro-2-ethylimidazo[2,1-a]isoquinoline

Product 1

HCID 54246393N-cyano-N'-(7-chloro-2-methylimidazo[2,1-a]isoquinolin-3-yl)formamidineYield 37.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-cyanoformimidate (3.2 g) was added to a suspension of 3-amino-7-chloro-2-ethylimidazo[2,1-a]isoquinoline (2.3 g) in ethanol (60 ml) and the mixture was stirred at room temperature for 45 hours. The mixture was evaporated in vacuo and the residual solid was washed successively with diethyl ether and ethyl acetate to give N-cyano-N'-(7-chloro-2-methylimidazo[2,1-a]isoquinolin-3-yl)formamidine (1.0 g).

Workup

  1. customThe mixture was evaporated in vacuo
  2. washthe residual solid was washed successively with diethyl ether and ethyl acetate

Sources & evidence

ORD record
ord-0d0c8a137f104508b1ecb4eeca710c3f
Source dataset
uspto-grants-1988_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04738967

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes