1-Isoquinolinamine → ethyl 4-imino-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate

HRID 1704819Notes

Reaction equation

HRID 1704819 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C(O[CH:15]=[C:16]([C:22]#[N:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>C(O)C>[NH:23]=[C:22]1[N:3]2[CH:4]=[CH:5][C:6]3[C:11]([C:2]2=[N:1][CH:15]=[C:16]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 2

HCID 737421-IsoquinolinamineHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 22758844ethyl 4-imino-4H-pyrimido[2,1-a]isoquinoline-3-carboxylateYield 67.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-aminoisoquinoline (14.4 g., 0.10 mole) and ethyl ethoxymethylenecyanoacetate (16.9 g., 0.10 mole) was plunged into an oil bath at 105°-110° and kept there for 10 minutes under a nitrogen atmosphere. During this time the mixture melted, evolved ethanol and set solid. The solid was crystallized from toluene to give bright yellow crystals (18 g., 67% yield) of ethyl 4-imino-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate, m.p. 197°-199°. Another recrystallization from toluene provided an analytical sample, m.p. 199°-201°.

Workup

  1. customwas plunged into an oil bath at 105°-110°
  2. customThe solid was crystallized from toluene

Sources & evidence

ORD record
ord-2a060bd6cabc43b1b7f7b671d8706318
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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