Acetic Anhydride → 7-acetyloxyimino-7H-indolizino[5,6,7-ij]isoquinoline

HRID 267993Notes

Reaction equation

HRID 267993 reaction equation
C([O:4][C:5](=[O:7])[CH3:6])(=O)C.O[N:9]=[C:10]1[C:24]2[C:25]3[C:20]([CH:21]=[CH:22][N:23]=2)=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]2[C:11]1=[CH:12][CH:13]=[CH:14]2>N1C=CC=CC=1>[C:5]([O:4][N:9]=[C:10]1[C:24]2[C:25]3[C:20]([CH:21]=[CH:22][N:23]=2)=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]2[C:11]1=[CH:12][CH:13]=[CH:14]2)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1363535147-hydroxyimino-7H-indolizino[5,6,7-ij]isoquinoline

Product 1

HCID 545331047-acetyloxyimino-7H-indolizino[5,6,7-ij]isoquinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

Acetic anhydride (20 cc.) is added, over the course of 5 minutes, to a stirred suspension of 7-hydroxyimino-7H-indolizino[5,6,7-ij]isoquinoline (10 g.) in pyridine (100 cc.) kept at between 8° and 10° C. A brown solution is thus obtained. After stirring for 5 minutes at 10° C., the acetic acid ester crystallises. The mixture is kept at ambient temperature for a further 2 hours and then water (600 cc.) is added. The ochre-yellow crystals thus obtained are filtered off and washed copiously with water. After drying, 7-acetyloxyimino-7H-indolizino[5,6,7-ij]isoquinoline (11.0 g.), melting at 177°-179° C. with decomposition, is obtained.

Workup

  1. customkept at between 8° and 10° C
  2. customA brown solution is thus obtained
  3. customthe acetic acid ester crystallises
  4. waitThe mixture is kept at ambient temperature for a further 2 hours
  5. additionwater (600 cc.) is added
  6. customThe ochre-yellow crystals thus obtained
  7. filtrationare filtered off
  8. washwashed copiously with water
  9. customAfter drying

Sources & evidence

ORD record
ord-2926b8c41f894844b43b72690683a296
Source dataset
uspto-grants-1976_03
Patent number
US03946019

Reaction notes

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