Water → Imidazo(1,2-b)isoquinoline, 5,10-dihydro-2-phenyl-

HRID 258995Notes

Reaction equation

HRID 258995 reaction equation
[Br-].[CH2:2]([N+:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.C([O-])(=O)C.[NH4+:25].O>C(O)(=O)C>[C:5]1([C:3]2[N:25]=[C:20]3[CH2:19][C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH2:12][N:11]3[CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 27948512-isoquinolinium-2-yl-1-phenylethan-1-one bromide

Product 1

HCID 3043511Imidazo(1,2-b)isoquinoline, 5,10-dihydro-2-phenyl-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-phenacylisoquinolinium bromide prepared as above (13.1 g) and ammonium acetate (28 g) in glacial acetic acid (36 ml) was heated under reflux for 2 hours. The cooled reaction mixture was poured, with stirring, into water (600 ml). The resultant solid was filtered off and washed well with water. The solid was dissolved in methanol (20 ml), and added dropwise, with stirring, to a solution of sodium hydroxide (1.6 g) in water (100 ml). A further 300 ml of water was added to the suspension, and the granulated solid filtered off, washed well with water, dried, and crystallised from methanol. Yield 2.1 g (21%) m.p. 195°-197°. (Found C 82.8; H 6.0; N 11.4, Required C 82.9; H 5.7; N 11.4).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe cooled reaction mixture
  4. additionwas poured
  5. filtrationThe resultant solid was filtered off
  6. washwashed well with water
  7. dissolutionThe solid was dissolved in methanol (20 ml)
  8. additionadded dropwise
  9. additionA further 300 ml of water was added to the suspension
  10. filtrationthe granulated solid filtered off
  11. washwashed well with water
  12. customdried
  13. customcrystallised from methanol

Sources & evidence

ORD record
ord-206ac72ea85047288168116f3ba6b248
Source dataset
uspto-grants-1977_07
Patent number
US04035499

Reaction notes

Loading…