Acetic Anhydride → HCID 19028832, compound

HRID 129227Notes

Reaction equation

HRID 129227 reaction equation
[N:1]([CH:4]1[CH2:33][C:8]2=[CH:9][N:10]([S:15]([C:18]3[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][C:21]([CH:27]([CH3:29])[CH3:28])=[CH:20][C:19]=3[CH:30]([CH3:32])[CH3:31])(=[O:17])=[O:16])[C:11]3[CH:12]=[CH:13][CH:14]=[C:6]([C:7]=32)[C:5]1=[O:34])=[N+]=[N-].[C:35](OC(=O)C)(=[O:37])[CH3:36]>C1COCC1.[Pd]>[C:35]([NH:1][CH:4]1[CH2:33][C:8]2=[CH:9][N:10]([S:15]([C:18]3[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][C:21]([CH:27]([CH3:29])[CH3:28])=[CH:20][C:19]=3[CH:30]([CH3:32])[CH3:31])(=[O:17])=[O:16])[C:11]3[CH:12]=[CH:13][CH:14]=[C:6]([C:7]=32)[C:5]1=[O:34])(=[O:37])[CH3:36]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 19028831HCID 19028831, compound

Product 1

HCID 19028832HCID 19028832, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-azido-3,4-dihydro-1-(2,4,6-triisopropylphenylsulfonyl)benz[cd]indol-5(1H)-one (5.36 g, 11.2 mmol), acetic anhydride (2.29 g, 22.4 mmol) and 10% Pd-C (1.7 g in THF (60 ml) was stirred for 4 hours at 4 hours under 4 atmospheres pressure under hydrogen atmosphere. After completion of the reaction, the catalyst was filtered off. The filtrate was concentrated under reduced pressure. To the concentrate was added isopropyl ether to give 5.03 g (91%) of the title compound.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionTo the concentrate was added isopropyl ether

Sources & evidence

ORD record
ord-3233c195d9e64a3faf9958f5e874c1b0
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

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