HCID 13689007, compound → HCID 13689009, compound

HRID 364165Notes

Reaction equation

HRID 364165 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11]([N+:15]([O-])=O)=[C:10]3[O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:8]([C:9]=23)=[N:7]1)[CH3:2].[H][H]>O1CCCC1.[Pd]>[NH2:15][C:11]1[CH:12]=[CH:13][C:14]2[N:6]([CH2:5][CH2:4][N:3]([CH2:25][CH3:26])[CH2:1][CH3:2])[N:7]=[C:8]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[O:18][C:10]=1[C:9]=23

Participants

5

Reactant 2

HCID 13689007HCID 13689007, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13689009HCID 13689009, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8.9 g (0.026 mole) of N,N-diethyl-5-nitro-2H-[1]benzopyrano[4,3,2-cd]indazole-2-ethanamine in 100 ml of tetrahydrofuran was hydrogenated over 1 g of 10% palladium on carbon at ambient temperature and a hydrogen pressure of 46.3-52.3 psi. The mixture was filtered and the solvent removed in vacuo. The oily residue was triturated with petroleum ether and recrystallized from n-hexane to give the product, mp 78°-80° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent removed in vacuo
  3. customThe oily residue was triturated with petroleum ether
  4. customrecrystallized from n-hexane
  5. customto give the product, mp 78°-80° C.

Sources & evidence

ORD record
ord-86b38c1c096a456a82b9d41015ad5920
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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