4-Hydroxyxylidine → 1-[4-acetyl-1-(4-hydroxy-2,3-dimethyl-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone

HRID 2375405Notes

Reaction equation

[C:1]([CH:4]([C:12](=O)[CH3:13])[CH:5]([C:9](=[O:11])[CH3:10])[C:6](=O)[CH3:7])(=[O:3])[CH3:2].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[C:17]=1[CH3:24]>>[C:9]([C:5]1[C:4]([C:1](=[O:3])[CH3:2])=[C:12]([CH3:13])[N:15]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[C:17]=2[CH3:24])[C:6]=1[CH3:7])(=[O:11])[CH3:10]

Participants

Reactant 2

HCID 765424-Hydroxyxylidine

HCID 787303,4-Diacetyl-2,5-hexanedione

Product 1

HCID 692752881-[4-acetyl-1-(4-hydroxy-2,3-dimethyl-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone

Procedure

Utilizing the general procedure outlined in Example 48, 1,1,2,2-tetraacetylethane (300 mg, 1.5 mol) and 4-amino-2.3-xylenol (206 mg, 1.5 mmol) reacted to give 1-[4-acetyl-1-(4-hydroxy-2,3-dimethyl-phenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-ethanone as yellow solid: MS (ESI) 300 (M+H)+.

Workup

customreacted

Sources & evidence

ORD record: ord-8cf72aeb103043469de7829dfe57a48e
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465730B2

Reaction notes

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