Methanol → HCID 178469031, compound

HRID 1788406Notes

Reaction equation

HRID 1788406 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].C(N(CC)CC)C.Cl.[NH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([OH:31])[CH2:27][CH2:26]1.CO>C(#N)C.O>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH:24][C@H:25]2[CH2:30][CH2:29][C@H:28]([OH:31])[CH2:27][CH2:26]2)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 1268247Ethyl 4-chloro-3-nitrobenzoateHCID 178479278HCID 178479278, compound

Product 1

HCID 178469031HCID 178469031, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 9 (689 mg, 3 mmol) was suspended in acetonitrile (5 mL) and then triethylamine was added (1.3 mL, 9 mmol). trans-4-aminocyclohexanol hydrochloride (682 mg, 4.5 mmol) was then added and the reaction refluxed for 12 hours, 2 mL methanol was then added and the reaction further refluxed for another 24 hours. Water (100 mL) was added and the resulting precipitate filtered, washed 3 times with water and air-dried. The product was used without further characterization in the next step MS: 309.3 (M+H+).

Workup

  1. temperaturethe reaction refluxed for 12 hours
  2. customthe reaction
  3. temperaturefurther refluxed for another 24 hours
  4. filtrationthe resulting precipitate filtered
  5. washwashed 3 times with water
  6. customair-dried

Sources & evidence

ORD record
ord-281bf03bd1aa4c5aae79f22617d8f70f
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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