Hydrazine hydrate (1:1) → HCID 135465609, compound

HRID 2059128Notes

Reaction equation

HRID 2059128 reaction equation
O.NN.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2O[C:16]([CH3:29])=[C:17]([CH2:27][CH3:28])[C:18]3[C:19]=2[CH:20]=[C:21]([O:25][CH3:26])[C:22](=[O:24])[CH:23]=3)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].C1C2C=CC=CC=2CC=[N:32][N:31]=1>C(O)(=O)C.[OH-].[Na+]>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:14]2[C:19]3[CH:20]=[C:21]([O:25][CH3:26])[C:22]([OH:24])=[CH:23][C:18]=3[CH:17]([CH2:27][CH3:28])[C:16]([CH3:29])=[N:32][N:31]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 128681925H-2,3-BenzodiazepineHCID 13041058HCID 13041058, compound

Product 1

HCID 135465609HCID 135465609, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

34.5 ml of 98% hydrazine hydrate are added dropwise, within 5 minutes, to a stirred solution of 115 g (0.325 mole) of 1-(3,4-dimethoxyphenyl)-3-methyl-4-ethyl-7-methoxy-6H-2-benzopyran-6-one in 115 ml of glacial acetic acid. During this operation the solution is maintained at 80° to 100° C. The solution is immersed into a water bath (95° to 100° C.) for one hour, then it is diluted with 140 ml of 2% aqueous sodium hydroxide solution and cooled. The 5H-2,3-benzodiazepine derivative separates as a beige crystalline substance. The solids are filtered off, washed four times with 50 ml of water each and dried. 111.7 g of the crude product are obtained; m.p.: 210°-212° C. To purify the crude product it is dissolved in 223 ml of dimethyl formamide at 100° to 130° C., and the solution is decolorized with 2 g of activated carbon. The carbon is filtered off and washed thrice with 50 ml of dimethyl formamide each. The solution is filtered with 1300 ml of distilled water, whereupon the pure product separates in crystalline form. 110.35 g (94%) of the title compound are obtained; m.p.: 210°-212° C. According to gas chromatographical examination the purity grade of the product is above 99%. C21H24N2O4 =368.4.

Workup

  1. temperatureDuring this operation the solution is maintained at 80° to 100° C
  2. customThe solution is immersed into a water bath
  3. temperaturecooled
  4. filtrationThe solids are filtered off
  5. washwashed four times with 50 ml of water each and
  6. customdried
  7. custom111.7 g of the crude product are obtained
  8. customTo purify the crude product it
  9. dissolutionis dissolved in 223 ml of dimethyl formamide at 100° to 130° C.
  10. filtrationThe carbon is filtered off
  11. washwashed thrice with 50 ml of dimethyl formamide each
  12. filtrationThe solution is filtered with 1300 ml of distilled water, whereupon the pure product

Sources & evidence

ORD record
ord-509849de6bac44a6951d863d160234e7
Source dataset
uspto-grants-1982_03
Patent number
US04322346

Reaction notes

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