Sodium Hydroxide → HCID 21285203, compound

HRID 2231938Notes

Reaction equation

HRID 2231938 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:24][CH2:25][CH3:26])=[C:18]([O:21][CH2:22][CH3:23])[CH:19]=3)[CH:14]=[C:13]([CH2:27][O:28]C(=O)C)[N:12]=2)[CH:7]=[CH:8][C:9]=1[Cl:10])([O-:3])=[O:2].[OH-].[Na+]>>[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:24][CH2:25][CH3:26])=[C:18]([O:21][CH2:22][CH3:23])[CH:19]=3)[CH:14]=[C:13]([CH2:27][OH:28])[N:12]=2)[CH:7]=[CH:8][C:9]=1[Cl:10])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 21285204HCID 21285204, compound

Product 1

HCID 21285203HCID 21285203, compound

Procedure

4.98 g (0.0112 M) of 1-(3-nitro-4-chlorophenyl)-3-(acetoxymethyl)-6,7-diethoxy-isoquinoline is refluxed with 50 ml of a 10% aqueous sodium hydroxide solution for 5 hours. During the hydrolysis the product is precipitated . The suspension formed is cooled, filtered, washed with water to remove sodium hydroxide, and dried. The crude product (4.27 g) is purified by treating it with 45 ml of hot, anhydrous ethanol, the suspension is cooled with ice-water, filtered, washed with 3×5 ml of anhydrous ethanol and dried. Yield 3.94 g (87.4%), m. p. 187° to 188° C.

Workup

  1. customDuring the hydrolysis the product
  2. customis precipitated
  3. customThe suspension formed
  4. temperatureis cooled
  5. filtrationfiltered
  6. washwashed with water
  7. customto remove sodium hydroxide
  8. customdried
  9. customThe crude product (4.27 g) is purified
  10. additionby treating it with 45 ml of hot, anhydrous ethanol
  11. temperaturethe suspension is cooled with ice-water
  12. filtrationfiltered
  13. washwashed with 3×5 ml of anhydrous ethanol
  14. customdried

Sources & evidence

ORD record
ord-4b177ea94ba24259b39e70a48b07ba0e
Source dataset
uspto-grants-1988_11
Patent number
US04785104

Reaction notes

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