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Hydroxyamine hydrochloride → 3-Amino-6-methoxy-5-(trifluoromethyl)pyridine-2-carboxylic acid

HRID 444927
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HRID 444927 반응식
CC1[N:3]([C:8]2[C:9]([C:20]([OH:22])=[O:21])=[N:10][C:11]([O:18][CH3:19])=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)C(C)=CC=1.Cl.NO>CCO.O.CCOC(C)=O>[NH2:3][C:8]1[C:9]([C:20]([OH:22])=[O:21])=[N:10][C:11]([O:18][CH3:19])=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=1
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참가 물질

6

반응물 2

HCID 443297Hydroxyamine hydrochlorideHCID 584423133-(2,5-Dimethyl-pyrrol-1-yl)-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid

생성물 1

HCID 584423203-Amino-6-methoxy-5-(trifluoromethyl)pyridine-2-carboxylic acid

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매
HCID 8857
Ethyl Acetate
용매

실험 절차

3-(2,5-Dimethyl-pyrrol-1-yl)-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid (2.1 g, 6.68 mmol) was dissolved in EtOH (40 ml) and water (20 ml). To this mixture was added TEA (2.79 ml, 20.05 mmol) followed by hydroxylamine hydrochloride (4.64 g, 66.8 mmol). The resulting mixture was heated at reflux for 5 hours. After cooling to RT, the mixture was diluted with EtOAc (100 ml) and washed with aqueous HCl (1M, 100 ml). The aqueous phase was back extracted with EtOAc (100 ml) and the combined organic phases washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to afford the product as an orange solid. The material can be used crude or recrystallised from isohexane-EtOAc (10:1) LC-MS Rt=1.0 min [M+H]+ 237 (Method 2 minLC_v003)

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 5 hours
  3. washwashed with aqueous HCl (1M, 100 ml)
  4. extractionThe aqueous phase was back extracted with EtOAc (100 ml)
  5. washthe combined organic phases washed with brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-8499f83a29414c53846df7ab1c2f5417
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08476269B2

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