Hydroxylamine → 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-hydroxypicolinamide

HRID 336421

반응식

HRID 336421 반응식
[NH2:1][OH:2].[NH2:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[C:11]=2[F:19])[N:7]=[C:6]([C:20](OC)=[O:21])[C:5]=1[Cl:24]>COCCOC>[NH2:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][CH3:18])[C:11]=2[F:19])[N:7]=[C:6]([C:20]([NH:1][OH:2])=[O:21])[C:5]=1[Cl:24]

참가 물질

4

반응물 2

HCID 787HydroxylamineHCID 16656802Halauxifen-methyl

생성물 1

HCID 594712974-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-N-hydroxypicolinamide수율 103.2%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
23 °C

실험 절차

A 50% aq solution of hydroxylamine (4.4 mL, 72 mmol, 50 equiv) was added to a stirred suspension of methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate (500 mg, 1.4 mmol, 1.0 equiv) in 1,2-dimethoxyethane (1.0 mL) at 23° C. The resulting white suspension was stirred at 23° C. for 4 days (d). The reaction mixture was concentrated by rotary evaporation to afford a white powder (500 mg, 99%): mp 166-169° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.19 (br s, 1H), 7.68 (t, J=8 Hz, 1H), 7.42 (m, 1H), 7.20 (m, 1H), 6.73 (br s, 2H), 6.53 (br s, 1H), 3.93 (s, 3H); IR (neat film) 3322 (m), 2941 (w), 2878 (w), 1653 (s), 1632 (s) cm−1; ESIMS m/z 346.2 ([M+H]+).

후처리

  1. concentrationThe reaction mixture was concentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-063e4644ba5e4493a9ec153474768cea
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889694B2

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