Hydrazine → HCID 131714816, compound

HRID 364211Notes

Reaction equation

HRID 364211 reaction equation
[ClH:1].[CH2:2]([N:4]([CH2:38][CH3:39])[CH2:5][CH2:6][N:7]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:17](=[O:30])[CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)=[C:11]3[S:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[C:9]([C:10]=23)=[N:8]1)[CH3:3].NN>CO>[ClH:1].[ClH:1].[NH2:19][CH2:18][C:17]([NH:16][C:12]1[CH:13]=[CH:14][C:15]2[N:7]([CH2:6][CH2:5][N:4]([CH2:2][CH3:3])[CH2:38][CH3:39])[N:8]=[C:9]3[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[S:31][C:11]=1[C:10]=23)=[O:30]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 131714817HCID 131714817, compound

Product 1

HCID 131714816HCID 131714816, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3 g of N-[2-[2-(Diethylamino)ethyl]-2H-[1]benzothiopyrano[4,3,2-cd]indazol-5-yl]-1,3-dihydro-1,3-dioxo-2H-isoindol-2-acetamide, monohydrochloride, prepared as described in Example 96A, 0.784 ml of 54% aqueous hydrazine, and 40 ml of methanol was stirred for 2 days. The solution was then evaporated to dryness and the residue was diluted with water and extracted three times with 35-ml portions of ethyl acetate. The combined extracts were washed with 25 ml of saturated aqueous sodium carbonate solution and then dried over anhydrous magnesium sulfate. The ethyl acetate solutions were evaporated to afford the title compound as the free base. The dihydrochloride salt crystallizes from a methanolic solution of the free base upon acidification with 2.25 equivalents of hydrochloric acid.

Workup

  1. customprepared
  2. customThe solution was then evaporated to dryness
  3. additionthe residue was diluted with water
  4. extractionextracted three times with 35-ml portions of ethyl acetate
  5. washThe combined extracts were washed with 25 ml of saturated aqueous sodium carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe ethyl acetate solutions were evaporated

Sources & evidence

ORD record
ord-9051ca7b8edf4e15b82f0db800a9ce01
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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