Methanol → HCID 69677721, compound

HRID 1816758Notes

Reaction equation

HRID 1816758 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][C@H:15]([CH3:17])[O:14][C@H:13]([CH3:18])[CH2:12]2)=[CH:7][CH:6]=1)C.CO.O1CCCC1.O.[NH2:28][NH2:29]>C(OCC)(=O)C.O>[CH3:18][C@H:13]1[O:14][C@@H:15]([CH3:17])[CH2:16][N:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([NH:28][NH2:29])=[O:3])=[CH:6][CH:7]=2)[CH2:12]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)2×HCID 53637089HCID 53637089, compound

Product 1

HCID 69677721HCID 69677721, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(cis-2,6-dimethylmorpholin-4-yl)benzoic acid ethyl ester (0.55 g) in a mixed solvent of methanol (3 ml) and tetrahydrofuran (6 ml) was added hydrazine monohydrate (1.6 ml). The solution was refluxed for 20 hours, during which period additional hydrazine monohydrate (1.6 ml) was added to the mixture. After cooling to ambient temperature, the reaction mixture was added to a mixture of water and ethyl acetate. The organic layer was washed with sodium chloride solution. The organic layer was taken and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was concentrated under reduced pressure to give 4-(cis-2,6-dimethylmorpholin-4-yl)benzoic acid hydrazide (489.7 mg).

Workup

  1. additionwas added to the mixture
  2. washThe organic layer was washed with sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bf83582fd3f34a07af32db04b838af68
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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