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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 1788932
Notes
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Reaction equation

HRID 1788932 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[CH3:23])=[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 201424413-Amino-7-chloro-2-methylimidazo[2,1-a]isoquinoline

Product 1

HCID 54246393N-cyano-N'-(7-chloro-2-methylimidazo[2,1-a]isoquinolin-3-yl)formamidineYield 35.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-cyanoformimidate (3.2 g) was added to a suspension of 3-amino-7-chloro-2-methylimidazo[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-f3890f0223094eaf9a2ee3e8c44021d2
Source dataset
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04686227

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes