4-Tert-Butylaniline → 2-[2-(4-Tert-butyl-phenylamino)-ethyl]-6-nitro-benzoic acid methyl ester

HRID 133110노트

반응식

HRID 133110 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([CH2:10][CH:11]=O)=[CH:8][CH:7]=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14].[C:17]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:5]([N+:13]([O-:15])=[O:14])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][CH2:11][NH:25][C:24]1[CH:26]=[CH:27][C:21]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 698614-Tert-ButylanilineHCID 5049666Sodium triacetoxyborohydrideHCID 866906922-Nitro-6-(2-oxoethyl)benzoic Acid Methyl Ester

생성물 1

HCID 691591522-[2-(4-Tert-butyl-phenylamino)-ethyl]-6-nitro-benzoic acid methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the aldehyde (Step B, 0.51 g, 2.3 mmol, 1 eq) and CH2Cl2 (30 mL) was added 4-t-butyl-aniline (0.36 mL, 2.3 mmol, 1 eq) and NaBH(OAc)3 (1.5 g, 6.8 mmol, 3.0 eq). The mixture was stirred at RT for 18 h then quenched with H2O. The mixture was extracted with EtOAc, the organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give an orange oil. Purification by silica flash chromatography gave the desired compound as a yellow-orange foam. MS m/e 357 (M+H)+. Calc'd for C20H24N2O4-356.42.

후처리

  1. customthen quenched with H2O
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give an orange oil
  7. customPurification by silica flash chromatography

출처 및 근거

ORD 기록
ord-19c51f58e8fc491a97da71dd17bc8f8c
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390820B2

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