Cyclohexanone → HCID 21477003, compound

HRID 2293526Notes

Reaction equation

HRID 2293526 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[Cl:11][C:10]1[C:2]([NH:1][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:3][C:4]([O:12][CH3:13])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21477003HCID 21477003, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a stream of argon, 3.08 g of 4-amino-5-chloro-2-methoxybenzoic acid and 1.00 g of cyclohexanone were added to 30 ml of acetic acid at room temperature, 4.30 g of sodium triacetoxyborohydride was added in small portions to the above solution, and then the resulting mixture was stirred for 1 hour. After completion of the reaction, the solvent was evaporated and the resulting residue was mixed with water, extracted with chloroform and then washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1-50:1) to give 0.37 g of 5-chloro-4-cyclohexylamino-2-methoxybenzoic acid.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionthe resulting residue was mixed with water
  4. extractionextracted with chloroform
  5. washwashed with saturated brine
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. customthe solvent was evaporated under a reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1-50:1)

Sources & evidence

ORD record
ord-4fa1dd61371e41f3bc7f91282528a4d0
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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