Diethyl Ether → HCID 19771012, compound

HRID 1589830Notes

Reaction equation

HRID 1589830 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[C:8]2Cl.[NH2:14][C:15]1[C:16]([CH3:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.CCOCC>C1(OC)C=CC=CC=1.CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[C:8]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 7242O-ToluidineHCID 218897871-Chloro-5-methoxyisoquinoline

Product 1

HCID 19771012HCID 19771012, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7519AnisoleSolvent

Procedure

5-Methoxy-1-chloroisoquinoline (1.5 g, 0.00777 mol) and o-toluidine (0.835 gm, 0.00777 mol) were mixed in anisole (10 ml) and heated with stirring in an oil-bath at 140° for four hours. After cooling the mixture was dissolved in methanol and ether was added to precipitate a tacky solid. The solvent was decanted off and the precipitate washed with more ether. The insoluble residue was equilibrated between N. HCl and ether, the aqueous acid solution filtered and basified with saturated aqueous Na2CO3 to precipitate a buff solid which was collected, washed with water and dried (0.77 g). This material was crystallised from diethyl ether to give the title compound (0.62 g) as fluffy, light-buff needles, m.p. 111°-112°.

Workup

  1. temperatureheated
  2. temperatureAfter cooling the mixture
  3. customto precipitate a tacky solid
  4. customThe solvent was decanted off
  5. washthe precipitate washed with more ether
  6. filtrationHCl and ether, the aqueous acid solution filtered
  7. customto precipitate a buff solid which
  8. customwas collected
  9. washwashed with water
  10. customdried (0.77 g)
  11. customThis material was crystallised from diethyl ether

Sources & evidence

ORD record
ord-f89465d4139b467a88ced938f6bbb12c
Source dataset
uspto-grants-1993_04
Patent number
US05200417

Reaction notes

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