Propionic anhydride → HCID 21285200, compound

HRID 2231940Notes

Reaction equation

HRID 2231940 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[C:14]([CH2:25][CH3:26])=[C:13]([CH3:27])[N+:12]=2[O-])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:29]([O:33]C(=O)CC)(=[O:32])[CH2:30][CH3:31]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[C:14]([CH2:25][CH3:26])=[C:13]([CH2:27][O:33][C:29](=[O:32])[CH2:30][CH3:31])[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 31263Propionic anhydrideHCID 54041025HCID 54041025, compound

Product 1

HCID 21285200HCID 21285200, compound

Procedure

3.83 g (10 mM) of 1-(3,4-dimethoxyphenyl)-3-methyl-4-ethyl-6,7-dimethoxy-isoquinoline N-oxide is refluxed with 20 ml of propionic anhydride for 1.5 hours. The solution is evaporated at reduced pressure, the residue is suspended in 100 ml of water, filtered, washed with 3×15 ml of water, dried at reduced pressure at room temperature, recrystallized from 7 ml of 99.5% ethanol, filtered, washed with 3×8 ml of ethanol and dried at 80° to 90° C. Yield 2.70 g (61.5%), m.p. 125° to 127° C.

Workup

  1. customThe solution is evaporated at reduced pressure
  2. filtrationfiltered
  3. washwashed with 3×15 ml of water
  4. customdried at reduced pressure at room temperature
  5. customrecrystallized from 7 ml of 99.5% ethanol
  6. filtrationfiltered
  7. washwashed with 3×8 ml of ethanol
  8. customdried at 80° to 90° C

Sources & evidence

ORD record
ord-bdae3950a1b04110845f22e00489ca75
Source dataset
uspto-grants-1988_11
Patent number
US04785104

Reaction notes

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