spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] → 2'-Amidinospiro[benzofuran-2(3H),4'(2'H)-isoquinoline] nitrate

HRID 648100Notes

Reaction equation

HRID 648100 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[CH2:3][NH:2]1.[N+:19]([O-:22])([OH:21])=[O:20].CC1([C:30]([NH2:32])=[NH:31])C=C(C)N=N1>C(O)C>[N+:19]([O-:22])([OH:21])=[O:20].[C:30]([N:2]1[CH2:3][C:4]2([CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[O:11]2)[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)(=[NH:31])[NH2:32]

Participants

4

Reactant 2

HCID 15917444spiro[benzofuran-2(3H),4'(2'H)-isoquinoline]HCID 694865753,5-Dimethylpyrazole carboxamidine nitrate

Product 1

HCID 159174722'-Amidinospiro[benzofuran-2(3H),4'(2'H)-isoquinoline] nitrateYield 42.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of spiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (4.2 g), 3,5-dimethylpyrazole carboxamidine nitrate (3.6 g) in 95% ethanol (80 ml) is heated under reflux for 7 hours. The mixture is evaporated to dryness in vacuo and the viscous residue is triturated with ether. After filtration, the precipitate is twice recrystallized from ethyl acetate/methanol to yield product (2.6 g, 42%) as a solid, mp 188°.

Workup

  1. temperatureunder reflux for 7 hours
  2. customThe mixture is evaporated to dryness in vacuo
  3. customthe viscous residue is triturated with ether
  4. filtrationAfter filtration
  5. customthe precipitate is twice recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-e0247224afea448a9ed5906181d1c00e
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

Loading…