Acetohydrazide → 2'-Acetylamino-6'-(2-hydroxypropyl)-3'-methoxy-4-nitrobenzophenone acetylhydrazone

HRID 2179898Notes

Reaction equation

HRID 2179898 reaction equation
C(N[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[C:11](O)([C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)[O:10][CH:9]([CH3:27])[CH2:8]2)(=O)C.[C:28]([NH:31][NH2:32])(=[O:30])[CH3:29]>C(O)C.Cl>[C:28]([NH:31][N:32]=[C:11]([C:12]1[C:7]([CH2:8][CH:9]([OH:10])[CH3:27])=[CH:6][CH:5]=[C:14]([O:15][CH3:16])[C:13]=1[NH:31][C:28](=[O:30])[CH3:29])[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)(=[O:30])[CH3:29]

Participants

5

Reactant 2

HCID 14039AcetohydrazideHCID 224889686-Acetylamino-1-hydroxy-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Product 1

HCID 865844732'-Acetylamino-6'-(2-hydroxypropyl)-3'-methoxy-4-nitrobenzophenone acetylhydrazoneYield 86.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of 22 (1.7 g) in 25 ml of ethanol was added acetic hydrazide (0.5 g) and 2 drops of concentrated HCl. The resulting solution was refluxed for 3 hours. The solvent was removed under reduced pressure. The residue was treated with NaHCO3, and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over Na2SO4. Removal of the solvent gave the desired product 23 (1.25 g).

Workup

  1. temperatureThe resulting solution was refluxed for 3 hours
  2. customThe solvent was removed under reduced pressure
  3. additionThe residue was treated with NaHCO3
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-8ee4d3da0e57482d9f98599d67594ed5
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

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