Trifluoroacetic acid → HCID 39417231, compound

HRID 1633956Notes

Reaction equation

HRID 1633956 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][CH:5]=1.[C:13]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].C(O)(C(F)(F)F)=O.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:21][C:20]2[CH:22]=[CH:23][C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:18][CH:19]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 15294Methyl 4-FormylbenzoateHCID 698614-Tert-ButylanilineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 39417231HCID 39417231, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Formylbenzoic acid methyl ester (10.6 g, 64 mmol) was dissolved in methanol (200 mL). 4-tert-Butylaniline (9.61 g, 64 mmol) was added and the resulting suspension was refluxed for 15 minutes. After cooling to room temperature, TFA (5.18 mL, 68 mmol) was added followed by portion wise addition of sodium cyanoborohydride (3.26 g, 52 mmol). The resulting mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was partitioned between ethyl acetate (200 mL) and 1N aqueous sodium hydroxide (150 and 100 mL). The organic phase was dried (MgSO4) and evaporated in vacuo to afford 19.0 g, (99%) of 4-[(4-tert-butylphenylamino)methyl]benzoic acid methyl ester as a solid.

Workup

  1. temperaturethe resulting suspension was refluxed for 15 minutes
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate (200 mL) and 1N aqueous sodium hydroxide (150 and 100 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-af772120afba42d5a3051202074feed2
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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