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

HRID 133110Notes

Reaction equation

HRID 133110 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-19c51f58e8fc491a97da71dd17bc8f8c
Source dataset
uspto-grants-2008_06
Patent number
US07390820B2

Reaction notes

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