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Hydrochloric Acid → 5-Chloro-3-[(2,6-difluorobenzyl)oxy]pyridine-2-amine

HRID 2401630
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HRID 2401630 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])[C:5]([N+:8]([O-])=O)=[N:6][CH:7]=1.Cl.C([O-])(=O)C.[Na+]>C(O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[C:14]([F:20])=[CH:15][CH:16]=[CH:17][C:18]=2[F:19])[C:5]([NH2:8])=[N:6][CH:7]=1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 867178765-Chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine

생성물 1

HCID 867178775-Chloro-3-[(2,6-difluorobenzyl)oxy]pyridine-2-amine

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

59.7 g of 5-chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine (Example 13A; 199 mmol, 1 equivalent) were initially charged in 600 ml of ethanol, 34.4 g of iron powder (616 mmol, 3.1 equivalents) were added and the mixture was heated to reflux. 152 ml of concentrated hydrochloric acid were slowly added dropwise and the mixture was boiled at reflux for a further 30 min. The reaction mixture was cooled and stirred into an ice/water mixture. The resulting mixture was adjusted to pH 5 using sodium acetate, the solid obtained was filtered off, washed with water and air-dried and then dried under reduced pressure at 50° C. This gave 52.7 g (98% of theory) of the title compound.

후처리

  1. temperaturethe mixture was heated to reflux
  2. temperatureat reflux for a further 30 min
  3. temperatureThe reaction mixture was cooled
  4. customthe solid obtained
  5. filtrationwas filtered off
  6. washwashed with water
  7. customair-dried
  8. customdried under reduced pressure at 50° C

출처 및 근거

ORD 기록
ord-7c8c5992aaa64a64af8b1b987d96572d
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08796305B2

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