Acetic Anhydride → 1-[1-(3-Chloro-4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

HRID 2375381Notes

Reaction equation

HRID 2375381 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH3:10].[C:18](OC(=O)C)(=[O:20])[CH3:19].I>>[C:18]([C:14]1[CH:13]=[C:12]([CH3:17])[N:11]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH3:10])=[C:2]([Cl:1])[CH:3]=2)[C:15]=1[CH3:16])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 24841Hydrogen iodideHCID 692753471-(3-Chloro-4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrole

Product 1

HCID 692753861-[1-(3-Chloro-4-ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

Procedure

Utilizing the general procedure outlined in EXAMPLE 1, 1-(3-chloro-4-ethoxyphenyl)-2,5-dimethylpyrrole (1.21 g, 4.8 mmol), acetic anhydride (5 mL), and hydriodic acid (0.07 mL, 0.83 mmol) reacted to give 3-acetyl-1-(3-chloro-4-ethoxyphenyl)-2,5-dimethylpyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 7.21 (d, 1H), 7.04-6.98 (m, 2H), 6.29 (s, 1H), 4.17 (q, 2H), 2.41 (s, 3H), 2.30 (s, 3H), 1.98 (s, 3H), 1.52 (t, 3H); MS (ESI) 292 (M+H)+.

Workup

  1. customreacted

Sources & evidence

ORD record
ord-55e44ca75c1c4be29ca434c92869b3ef
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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