Hydrochloric Acid → HCID 21285205, compound

HRID 2231935Notes

Reaction equation

HRID 2231935 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([CH2:22][O:23]C(=O)C)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([CH2:22][OH:23])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 21285214HCID 21285214, compound

Product 1

HCID 21285205HCID 21285205, compoundYield 197.1%

Procedure

15.67 g (0.042 M) of 1-(3-chlorophenyl)-3-(acetoxymethyl)-6,7-dimethoxy-isoquinoline (compound of Example 21) are refluxed in 160 ml of an aqueous 5% solution of hydrochloric acid for one hour. The crystals of the end-product are rapidly beginning to form from the initially clear solution. After ice-cooling the reaction mixture is filtered, the product is washed with 3×10 ml of water and dried at 90° to 100° C., giving 15.21 g of a crude product, m.p. 210° to 214° C. The crude product is purified by refluxing in 180 ml of 99.5% ethanol, the suspension is cooled and kept at +5° C. for 10 hours, then it is filtered, washed with 3×5 ml of ethanol and dried. Yield 12.67 g (82.4%), m. p. 219° to 221° C. d.

Workup

  1. customto form from the initially clear solution
  2. temperatureAfter ice-cooling the reaction mixture
  3. filtrationis filtered
  4. washthe product is washed with 3×10 ml of water
  5. customdried at 90° to 100° C.

Sources & evidence

ORD record
ord-2281c3ffd73143878eb54da299daf204
Source dataset
uspto-grants-1988_11
Patent number
US04785104

Reaction notes

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