Acetic Acid → HCID 20303922, compound

HRID 1732592Notes

Reaction equation

HRID 1732592 reaction equation
[C:1]([N:4]1[C:12]2[C:11]([Cl:13])=[CH:10][CH:9]=[C:8]3[C:14](=[O:18])[CH:15](Br)[CH2:16][C:6]([C:7]=23)=[CH:5]1)(=[O:3])[CH3:2].C(O)(=O)C.[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C)C=O>[C:1]([N:4]1[C:12]2[C:11]([Cl:13])=[CH:10][CH:9]=[C:8]3[C:14](=[O:18])[CH:15]([N:23]=[N+:24]=[N-:25])[CH2:16][C:6]([C:7]=23)=[CH:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 33557Sodium AzideHCID 20303920HCID 20303920, compound

Product 1

HCID 20303922HCID 20303922, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-acetyl-4-bromo-8-chloro-3,4-dihydrobenz[cd]-indol-5(1H)-one (8.3 g., 0.029 mole) in dimethylformamide (70 ml.) containing 5 ml of acetic acid and cooled in an ice bath, is added a solution of sodium azide (3.8 g. in 17 ml. of H2O) at such a rate that the reaction temperature does not exceed 25° C. Stirring is continued for 1.5 hours with cooling. The reaction mixture is poured into water (200 ml.) and the dark solid that separates is recovered by filtration and dried. The yield of crude 1-acetyl-4-azido-8-chloro-3,4-dihydrobenz[cd]-indol-5(1H)-one is 7.0 g. (97%).

Workup

  1. temperaturecooled in an ice bath
  2. customdoes not exceed 25° C
  3. temperaturewith cooling
  4. filtrationthe dark solid that separates is recovered by filtration
  5. customdried

Sources & evidence

ORD record
ord-2879f48177624d18a6478ac22226dd91
Source dataset
uspto-grants-1980_12
Patent number
US04238486

Reaction notes

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