Acetaldehyde → HCID 22268711, compound

HRID 270233Notes

Reaction equation

HRID 270233 reaction equation
F[C:2](F)(F)[C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)[C:9]([O:11]C)=[O:10])=O.C(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1)[C:9]([OH:11])=[O:10])[CH3:2]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22268778HCID 22268778, compound

Product 1

HCID 22268711HCID 22268711, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-amino-5-(trifluoromethyl)benzoate (cf. procedures (116a) and (80a); 177 mg, 0.81 mmol) was dissolved in MeOH (12 mL) and the resulting solution was charged successively with acetaldehyde (0.045 mL, 0.81 mmol) and sodium cyanoborohydride (64 mg, 1.01 mmol). The reaction was stirred at RT for 12 h, concentrated in vacuo, and diluted with EtOAc. The organic phase was washed with sat. NaHCO3, water (2×), and brine before being dried (Na2SO4), filtered, and concentrated in vacuo. This product was dissolved in 3:1 THF/MeOH (12 mL) and the resultant solution was charged with lithium hydroxide (3 mL of a 1N solution). The reaction was stirred for 14 h, acidified with 1N HCl, and extracted with EtOAc (2×). The organic extracts were combined, washed with water, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide 3-ethylamino-5-(trifluoromethyl)benzoic acid.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with sat. NaHCO3, water (2×), and brine
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThis product was dissolved in 3:1 THF/MeOH (12 mL)
  8. additionthe resultant solution was charged with lithium hydroxide (3 mL of a 1N solution)
  9. stirringThe reaction was stirred for 14 h
  10. extractionextracted with EtOAc (2×)
  11. washwashed with water
  12. washwashed with brine
  13. dry with materialdried (Na2SO4)
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34dc56d670534d1fb5cef4993da818de
Source dataset
uspto-grants-2008_11
Patent number
US07449493B2

Reaction notes

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