Hydrochloric Acid → HCID 19771024, compound

HRID 1589829Notes

Reaction equation

HRID 1589829 reaction equation
CO[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[C:8]2[Cl:13].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:22]([O-:25])([O-])=O.[Na+].[Na+].Cl.[CH3:29]O>C(Cl)Cl>[ClH:13].[CH3:29][O:25][C:22]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:16]=1[CH:15]=[CH:14][N:21]=[C:8]2[NH:7][CH2:6][CH2:5][C:4]1[CH:3]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7504BenzylamineHCID 10340Sodium CarbonateHCID 218897871-Chloro-5-methoxyisoquinoline

Product 1

HCID 19771024HCID 19771024, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Methoxy-1-chloroisoquinoline (J.A.C.S. (1947), 69, 1939) (1.5 g, 0.00777 mol) and benzylamine (1.67 g, 0.0156 mol) were mixed at room temperature and heated, with stirring, in an oil-bath at 150° for 4 hours. After cooling the mixture was equilibrated between CH2Cl2 and aqueous Na2CO3. The CH2Cl2 fraction was washed with water, dried and evaporated to dryness. The oil produced was dissolved in the minimum amount of methanol and aqueous 2N. HCl added to precipitate a buff solid which was collected, washed with water and dried (2.15 g). This material was crystallised from ethanol/methanol to give the title compound (1.40 g) as its hydrochloride salt, m.p. 247°-252° (Dec).

Workup

  1. temperatureheated
  2. temperatureAfter cooling the mixture
  3. washThe CH2Cl2 fraction was washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe oil produced
  7. customto precipitate a buff solid which
  8. customwas collected
  9. washwashed with water
  10. customdried (2.15 g)
  11. customThis material was crystallised from ethanol/methanol

Sources & evidence

ORD record
ord-f7e4b4e2f81d4d469eb0f8ac5caa5d46
Source dataset
uspto-grants-1993_04
Patent number
US05200417

Reaction notes

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