Sodium Hydroxide → 4-[Amino(phenyl)methyl]phenol

HRID 962708

반응식

HRID 962708 반응식
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6](=[N:13]O)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+].[OH-].[Na+]>[Cl-].[Cl-].[Cl-].[Ti+3].C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([NH2:13])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:15][CH:16]=1

참가 물질

8

반응물 5

HCID 14798Sodium HydroxideHCID 973924-Hydroxybenzophenone oximeHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 49622034-[Amino(phenyl)methyl]phenol

시약·촉매·용매 2

HCID 10313229titanium(III) trichloride촉매HCID 8857Ethyl Acetate용매

실험 절차

A procedure similar to that described in Preparation 12 was repeated, but using 86 ml of a methanolic solution containing 4.28 g of 4-hydroxybenzophenone oxime, 17.03 g of ammonium acetate, 3.79 g of sodium cyanoborohydride, and 40.1 ml of a 17-19% by volume aqueous solution of titanium trichloride, and using a dilute aqueous solution of sodium hydrogencarbonate instead of the aqueous solution of sodium hydroxide, and using ethyl acetate as the extracting solvent. The residue obtained was subjected to silica gel column chromatography and eluted with a 80% by volume solution of ethyl acetate in hexane, with ethyl acetate itself and with a 3% by volume solution of methanol in ethyl acetate, to give 2.74 g of the title compound as crystals, melting at 113°-115° C. (after recrystallization from methylene chloride).

후처리

  1. customA procedure similar to that described in Preparation 12
  2. customThe residue obtained
  3. washeluted with a 80% by volume solution of ethyl acetate in hexane, with ethyl acetate itself and with a 3% by volume solution of methanol in ethyl acetate
  4. customto give
  5. custom2.74 g of the title compound as crystals, melting at 113°-115° C. (after recrystallization from methylene chloride)

출처 및 근거

ORD 기록
ord-7da5bf70670f46659e1bfa728624145f
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760025

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