Ammonium Chloride → Ethyl 2-amino-5-(benzyloxy)-4-fluorobenzoate

HRID 1022482노트

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HRID 1022482 반응식
[NH4+].[Cl-].[CH2:3]([O:10][C:11]1[C:12]([F:25])=[CH:13][C:14]([N+:22]([O-])=O)=[C:15]([CH:21]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.C(O)(C)C.C1COCC1>[NH2:22][C:14]1[CH:13]=[C:12]([F:25])[C:11]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:21][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

참가 물질

6

반응물 2

HCID 25517Ammonium Chloride2회HCID 67495361Ethyl 5-(benzyloxy)-4-fluoro-2-nitrobenzoate

생성물 1

HCID 61994641Ethyl 2-amino-5-(benzyloxy)-4-fluorobenzoate수율 82%

시약·촉매·용매 3

HCID 962Water용매HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

1.76 g of NH4Cl dissolved in 21 ml of water are added to a mixture heated to 90° C. of 7.0 g of the compound obtained in Step 4.1, and 4.44 g of Fe(0) in 400 ml of isopropanol and 100 ml of THF. The reaction mixture is heated for 4 hours at 90° C. A further 0.88 g of NH4Cl is added and the mixture is heated for 2 hours at 90° C. The resulting mixture is filtered while hot and the filtrate is evaporated under reduced pressure. The residue is taken up in EtOAc and washed twice with saturated NaHCO3 solution. The organic phase is dried over MgSO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a PE/EtOAc mixture from (100/0, v/v) to (40/60, v/v) to give 5.2 g of the expected product.

후처리

  1. additionare added to a mixture
  2. temperaturethe mixture is heated for 2 hours at 90° C
  3. filtrationThe resulting mixture is filtered while hot and the filtrate
  4. customis evaporated under reduced pressure
  5. washwashed twice with saturated NaHCO3 solution
  6. dry with materialThe organic phase is dried over MgSO4
  7. filtrationfiltered
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe residue is chromatographed on silica gel
  10. washeluting with a PE/EtOAc mixture from (100/0

출처 및 근거

ORD 기록
ord-9376898b46c241288c347f0fe15abec6
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722659B2

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