HCID 178526409, compound → HCID 178507218, compound

HRID 1165817Notes

Reaction equation

HRID 1165817 reaction equation
[OH:1][C:2]1[C:3]([OH:19])=[N:4][C:5]2[CH:6]=[C:7]([N+:16]([O-])=O)[C:8]3[CH2:15][CH2:14][CH2:13][CH2:12][C:9]=3[C:10]=2[N:11]=1>CN(C)C=O.[Pd]>[NH2:16][C:7]1[C:8]2[CH2:15][CH2:14][CH2:13][CH2:12][C:9]=2[C:10]2[N:11]=[C:2]([OH:1])[C:3]([OH:19])=[N:4][C:5]=2[CH:6]=1

Participants

4

Reactant 1

HCID 178526409HCID 178526409, compound

Product 1

HCID 178507218HCID 178507218, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 7,8,9,10-tetrahydro-2,3-dihydroxy-6-nitrobenzo(f)quinoxaline (1.5 g, 5.7 mmol) in 50 ml of N,N-dimethylformamide was hydrogenated at atmospheric pressure and room temperature in the presence of 5% palladium-on-charcoal. The catalyst was filtered off, and the filtrate was evaporated to dryness. The residue was triturated with water, the solid was collected and washed with water, and ethanol affording 1.2 g (90%) of the amino compound; m.p. > 300° C.; 1H-NMR (DMSO-d6): 1.7-2.0 (m,4H,2×CH2), 2.5-2.8 (m,4H, 2 × CH2), 4.97 (broad s, 2H, NH2), 6.53 (s, 1H, H-5), 10.5 (broad s, 1H, 0H), 11.4 (broad s, 1H, 0H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was triturated with water
  4. customthe solid was collected
  5. washwashed with water, and ethanol affording 1.2 g (90%) of the amino compound

Sources & evidence

ORD record
ord-4f0c63f83975423bb7958bdfa65f963d
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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