Hydrochloric Acid → Methyl 2-(4-amino-3-chlorophenyl)acetate

반응식

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[NH:8]C(=O)C.Cl.[CH3:17]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([O:15][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[NH2:8]

참가 물질

반응물 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 187019472-(3-Chloro-4-acetamidophenyl)acetic acid

생성물 1

HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

실험 절차

A solution of 3-chloro-4-acetamidophenylacetic acid (180 grams, 0.79 moles) in methanol (2 L), was treated with concentrated HCl (200 mL) and the resulting solution refluxed for 6 hours and then stirred at room temperature for 16 hours. The mixture was concentrated in vacuo to about one-half its volume and ether (4 L) was added. The resulting precipitate was filtered, washed with ether and dried to give the title compound (173 grams) as a tan solid NMR, (CD3OD): δ3.70 (s, 2H); 3.73 (s, 3H); 7.35 (d, 1H); 7.43 (d, 1H); 7.56 (s, 1H).

후처리

temperaturethe resulting solution refluxed for 6 hours
concentrationThe mixture was concentrated in vacuo to about one-half its volume and ether (4 L)
additionwas added
filtrationThe resulting precipitate was filtered
washwashed with ether
customdried

출처 및 근거

ORD 기록: ord-c6c9b7f353b942c9807c3fe0d847b28d
출처 데이터셋: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05859051

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