Acetic Acid → HCID 14156732, compound

HRID 579980Notes

Reaction equation

HRID 579980 reaction equation
C(O)(=O)C.[C-:5]#[N:6].[Na+].[CH2:8]1[N:19]2[C:20]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=[N:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=32)[CH2:9]1>C(OCC)(=O)C>[C:5]([CH:15]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]3[CH2:9][CH2:8][N:19]([C:20]=23)[C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[NH:16]1)#[N:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 125191331,2-Dihydroindolo[1,7-ab][1,5]benzodiazepine

Product 1

HCID 14156732HCID 14156732, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Acetic acid (30 ml) was added to a slurry consisting of sodium cyanide (10 g), 1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]-benzodiazepine (19 g) and ethyl acetate (250 ml) dropwise at room temperature. The mixture was stirred for 18 hours and thereafter diluted with ethyl acetate to 1 liter and washed with 1N sodium hydroxide (2×500 ml), water (2×600 ml) and brine (2×600 ml) The solution was dried over anhydrous magnesium sulfate and concentrated to a solid. The solid was triturated with ether (2×150 ml). Recrystallization from hot toluene (450 ml) yielded 14.8 g of crystals, m.p. 185°-186.5° C.

Workup

  1. washwashed with 1N sodium hydroxide (2×500 ml), water (2×600 ml) and brine (2×600 ml) The solution
  2. dry with materialwas dried over anhydrous magnesium sulfate
  3. concentrationconcentrated to a solid
  4. customThe solid was triturated with ether (2×150 ml)
  5. customRecrystallization from hot toluene (450 ml)

Sources & evidence

ORD record
ord-93c8ce5ca48d43848d92b6e137612d2d
Source dataset
uspto-grants-1988_06
Patent number
US04751223

Reaction notes

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