Acetic Acid → Methyl 5-bromo-3-(ethylamino)-2-methylbenzoate

HRID 1530269Notes

Reaction equation

HRID 1530269 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:14](=O)[CH3:15].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl>[Br:12][C:10]1[CH:11]=[C:2]([NH:1][CH2:14][CH3:15])[C:3]([CH3:13])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 24729181Methyl 3-Amino-5-bromo-2-methylbenzoate

Product 1

HCID 70872675Methyl 5-bromo-3-(ethylamino)-2-methylbenzoateYield 55%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (1.0 g, 4.09 mmol) and acetaldehyde (180 mg, 4.09 mmol) in dichloroethane (10 mL), acetic acid (1.47 g, 24.58 mmol) was added and reaction stored at room temperature for 30 minutes. Then sodium triacetoxyborohydride (2.6 g, 12.29 mmol) was added at 0° C., allowed to attain room temperature and stirring continued for 2 h. On completion, reaction mixture was diluted with dichloromethane, washed with water, saturated aqueous sodium bicarbonate solution and dried over sodium sulphate. Removal of the solvent under reduced pressure followed by column chromatographic purification afforded the desired compound (600 mg, 55%).

Workup

  1. customreaction
  2. customto attain room temperature
  3. waitcontinued for 2 h
  4. customOn completion, reaction mixture
  5. washwashed with water, saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over sodium sulphate
  7. customRemoval of the solvent under reduced pressure
  8. customfollowed by column chromatographic purification

Sources & evidence

ORD record
ord-9cb7ee0bb1d84ab890deb617e0a7c2d4
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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