p-Toluidine → P-Anisidine

HRID 2212804Notes

Reaction equation

HRID 2212804 reaction equation
C[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C[CH2:10][O:11]C(C)=O>>[CH3:10][O:11][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7813p-ToluidineHCID 8857Ethyl Acetate

Product 1

HCID 7732P-Anisidine

Procedure

Column chromatography was performed in the dark, using 50% EtOAc/50% hexanes as eluent. Three bands emerged; the first band was a fluorescent impurity, the second and third bands were the di-(rf˜0.7) and monomethyl aniline (rf˜0.65), respectively. Rotary evaporation of the middle fractions gave the product in modest yield (˜1 gram, 16% based on starting p-anisidine). The off-white solid was further purified by sublimation (high vacuum, heated at 30° C., collected on a small cold finger). Product isolated at this stage was sufficiently pure for reductive quenching purposes. Due to its short shelf-life (stored at 4° C., under argon, protected from light), the compound was frequently recrystallized from warm water before use. 1H NMR (CDCl3): δ 3.30 (s, N—CH3, 6H), 3.88 (s, O—CH3, 3H), 7.58 (d, 21), 7.15 (d, 21). GC-MS calcd for C9H13NO (M−H+) m/z 150, found 150.

Workup

  1. customRotary evaporation of the middle fractions
  2. customgave the product

Sources & evidence

ORD record
ord-2603b38e5b90465abb3c570cfef1dfa9
Source dataset
uspto-grants-2006_09
Patent number
US07105310B1

Reaction notes

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