N-[(furan-2-yl)methyl]acetamide → Aniline

HRID 1284551Notes

Reaction equation

HRID 1284551 reaction equation
C([NH:4][CH2:5][C:6]1O[CH:8]=[CH:9][CH:10]=1)(=O)C.[CH3:11][O:12][C:13]1([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[CH:17]=[CH:16][CH:15]([O:18][CH3:19])[O:14]1>C(O)(=O)C>[CH3:11][O:12][C:13]1([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[CH2:17][CH2:16][CH:15]([O:18][CH3:19])[O:14]1.[NH2:4][C:5]1[CH:6]=[CH:10][CH:9]=[CH:8][CH:11]=1

Participants

5

Reactant 2

HCID 2394850N-[(furan-2-yl)methyl]acetamide2×HCID 10987294HCID 10987294, compound2×

Product 2

HCID 6115AnilineHCID 10888981HCID 10888981, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Clauson-Kaas and Tyle [Acta Chem. Scand. 6, 667 (1952)] described the methoxylation of 2(acetamidomethyl)-furan (Formula II) to 2,5-dimethoxy-2(acetamidomethyl)-2,5-dihydrofuran (Formula III). This compound was hydrogenated with catalyst to give 2,5-dimethoxy-2(acetamidomethyl)-tetrahydrofuran (Formula IV), which with aniline in acetic acid medium gave 1-phenyl-2-(acetamidomethyl)-pyrrole (Formula V), with a mean yield of 81% according to the following scheme: ##STR4##

Sources & evidence

ORD record
ord-7107ce713328429d8899060472bc7fe7
Source dataset
uspto-grants-1986_01
Patent number
US04563477

Reaction notes

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