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

HRID 1616369Notes

Reaction equation

HRID 1616369 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].[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Br:12][C:10]1[CH:11]=[C:2]([NH:1][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:3]([CH3:13])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 24729181Methyl 3-Amino-5-bromo-2-methylbenzoate

Product 1

HCID 70872336Methyl 5-bromo-3-(cyclohexylamino)-2-methylbenzoateYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (5.0 g, 20.6 mmol) and cyclohexanone (4.03 g, 41.2 mmol) in methanol (50 mL), acetic acid (0.247 g, 20.6 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (1.55 g, 24.6 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford methyl 5-bromo-3-(cyclohexylamino)-2-methylbenzoate (2.75 g, 41%).

Workup

  1. customreaction
  2. customreaction
  3. stirringstirred overnight
  4. customOn completion, solvent was removed under reduced pressure and crude material
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-bad2cf5574174250aa3739713f319576
Source dataset
uspto-grants-2014_07
Patent number
US08765732B2

Reaction notes

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