Benzoyl chloride → 1-(benzoyloxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H,4H-[1,3]oxazino-[4,3-a]isoquinoline

HRID 1731736Notes

Reaction equation

HRID 1731736 reaction equation
[OH:1][CH2:2][CH:3]1[CH:8]2[C:9]3[C:14]([CH2:15][CH2:16][N:7]2[CH2:6][O:5][CH2:4]1)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[C:21]([O:1][CH2:2][CH:3]1[CH:8]2[C:9]3[C:14]([CH2:15][CH2:16][N:7]2[CH2:6][O:5][CH2:4]1)=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 145953501-(hydroxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H,4H-[1,3]oxazino[4,3-a]isoquinoline

Product 1

HCID 145953651-(benzoyloxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H,4H-[1,3]oxazino-[4,3-a]isoquinolineYield 55%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.01 mole (2.79 g) of 1-(hydroxymethyl)-9,10-dimethoxy-1,6,7,11b-tetrahydro-2H,4H-[1,3]oxazino[4,3-a]isoquinoline in 30 ml of absolute pyridine is boiled with 0.012 mole (1.69 g) of benzoyl chloride for 3 hours. The mixture is then poured onto 100 g of ice. The separated crystals are filtered off, washed with water and recrystallized from a mixture of diisopropyl ether and ethanol. Yield: 55%. The melting point and spectroscopical data of the compound are identical with those of the product obtained in Example 25.

Workup

  1. filtrationThe separated crystals are filtered off
  2. washwashed with water
  3. customrecrystallized from a mixture of diisopropyl ether and ethanol

Sources & evidence

ORD record
ord-acf5eb8389604fd994c8f273983a2481
Source dataset
uspto-grants-1986_11
Patent number
US04623647

Reaction notes

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