Acetyl chloride → 1-(6-amino-1H-indol-1-yl)ethanone

HRID 423735Notes

Reaction equation

HRID 423735 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O.[C:13](Cl)(=[O:15])[CH3:14]>CC#N>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[C:13](=[O:15])[CH3:14])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 785026-Nitro-1H-indole

Product 1

HCID 222777891-(6-amino-1H-indol-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(6-Amino-indol-1-yl)-ethanone (B-3) was synthesized following the general scheme above starting from 6-nitroindole and acetyl chloride. Overall yield (˜40%). HPLC ret. time 0.54 min, 10-99% CH3CN, 5 min run; ESI-MS 175.1 m/z (MH+).

Workup

  1. customOverall yield (˜40%)

Sources & evidence

ORD record
ord-10368cb2b0904b71a50ae8b7ebce6408
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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