Ammonia → HCID 22278602, compound

HRID 1063096Notes

Reaction equation

HRID 1063096 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]2[C:12]3[C:17]([C:18]([CH2:19][C:20]#[N:21])=[C:4]2[NH:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=3.CO.N>CN(C=O)C.C(O)C.[Ni]>[NH2:21][CH2:20][CH2:19][C:18]1[C:17]2[C:12]([N:5]3[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:2](=[O:1])[NH:3][C:4]=13)=[CH:13][CH:14]=[CH:15][CH:16]=2

Participants

7

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 22278600HCID 22278600, compound

Product 1

HCID 22278602HCID 22278602, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

(5-Oxo-5,6-dihydro-indolo[1,2-a]quinazoline-7-yl)-acetonitrile (0.5 g, 1.83 mmol) (example 15) is dissolved in DMF (25 ml) and MeOH with 10% NH3 (25 ml) and catalytically hydrogenolized with Raney-Nickel (0.2 g) in ethanol at 50° C. for 9 h. The catalyst is removed by filtration. The product spontaneously crystallizes from the filtrate giving 0.23 mg (46%) slightly greenish crystals. m.p.: >300° C. ES-MS(+): 278 (M+1).

Workup

  1. customThe catalyst is removed by filtration
  2. customThe product spontaneously crystallizes from the filtrate
  3. customgiving 0.23 mg (46%) slightly greenish crystals

Sources & evidence

ORD record
ord-37a2637ff04741e0ace8cf43cc185394
Source dataset
uspto-grants-2005_11
Patent number
US06964960B2

Reaction notes

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