Trifluoroacetic acid → HCID 39417231, compound

HRID 967640Notes

Reaction equation

HRID 967640 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 99.8%

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 min. 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 1 N aqueous sodium hydroxide (150 and 100 mL). The organic phase was dried (magnesium sulphate) 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 min
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate (200 mL) and 1 N aqueous sodium hydroxide (150 and 100 mL)
  4. dry with materialThe organic phase was dried (magnesium sulphate)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-615fa7ac21934c1bbbdff7376cc63068
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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