6-Chloro-5-methylpyridin-3-amine → 6-Chloro-5-methylpyridin-3-ol

HRID 1160867

반응식

HRID 1160867 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5](N)=[CH:4][C:3]=1[CH3:9].N([O-])=[O:11].[Na+]>Cl.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:11])=[CH:4][C:3]=1[CH3:9]

참가 물질

5

반응물 2

HCID 122956076-Chloro-5-methylpyridin-3-amineHCID 23668193Sodium Nitrite

생성물 1

HCID 128520156-Chloro-5-methylpyridin-3-ol수율 33.6%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

2-Chloro-3-methyl-5-nitro-pyridine (2 g, 11.6 mmol) and SnCl2.(H2O)2 (7.86 g, 34.8 mmol) are refluxed in MeOH overnight. After cooled down, the mixture is diluted with ethyl acetate, washed with water, brine, dried over MgSO4, concentrated and purified by column chromatography to afford 6-chloro-5-methyl-pyridin-3-ylamine (1.7 g). To the solution of 6-chloro-5-methyl-pyridin-3-ylamine (1.7 g, 11.6 mmol) in 1N HCl is added the solution of NaNO2 (960 mg, 13.92 mmol) in water (10 ml) slowly at 0° C. After the addition, the solution is stirred for 20 min and then heated to 90° C. for 30 min. The solution is cooled down, quenched with K2CO3, extracted with ether, dried over MgSO4, and purified by column chromatography to afford the titled compound (560 mg) as a yellow solid.

후처리

  1. additionAfter the addition
  2. temperatureThe solution is cooled down
  3. customquenched with K2CO3
  4. extractionextracted with ether
  5. dry with materialdried over MgSO4
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-e2fa8982622b497c9f05cb38ac64b48d
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816557B2

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