2,5-Hexanedione → 2-chloro-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzenol

HRID 2375379Notes

Reaction equation

HRID 2375379 reaction equation
[CH2:1]([CH2:5][C:6](=O)[CH3:7])[C:2]([CH3:4])=O.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([Cl:17])[CH:11]=1>>[Cl:17][C:12]1[CH:11]=[C:10]([N:9]2[C:6]([CH3:7])=[CH:5][CH:1]=[C:2]2[CH3:4])[CH:15]=[CH:14][C:13]=1[OH:16]

Participants

3

Reactant 2

HCID 80352,5-HexanedioneHCID 775784-Amino-2-chlorophenol

Product 1

HCID 27645522-chloro-4-(2,5-dimethyl-1H-pyrrol-1-yl)benzenol

Procedure

Utilizing the general procedure outlined in EXAMPLE 1, acetonyl acetone (0.83 mL, 7.0 mmol) and 4-amino-2-chlorophenol (1.0 g, 7.0 mmol) reacted to give 1-(3-chloro-4-hydroxyphenyl)-2,5-dimethylpyrrole as a brown solid: 1H NMR (CDCl3, 500 MHz) δ 7.22 (d, 1H), 7.10 (d, 1H), 7.05 (dd, 1H), 5.88 (s, 2H), 5.66 (br s, 1H), 2.03 (s, 6H); MS (ESI) 222 (M+H)+.

Workup

  1. customreacted

Sources & evidence

ORD record
ord-e4d858a8e7694ce38ca4b4f5f526bcb5
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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