Hydrochloric Acid → HCID 178516988, compound

HRID 1165815Notes

Reaction equation

HRID 1165815 reaction equation
[OH:1][C:2]1[C:3]([OH:22])=[N:4][C:5]2[CH:6]=[C:7]([N+]([O-])=O)[C:8]3[CH:15]=[CH:14][CH:13]=[C:12]([N+]([O-])=O)[C:9]=3[C:10]=2[N:11]=1.Cl.O.O.C(O)(=O)C(O)=O>>[OH:1][C:2]1[C:3]([OH:22])=[N:4][C:5]2[CH:6]=[CH:7][C:8]3[CH2:15][CH2:14][CH2:13][CH2:12][C:9]=3[C:10]=2[N:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 61373Oxalic acid dihydrateHCID 178526411HCID 178526411, compound

Product 1

HCID 178516988HCID 178516988, compound

Procedure

A suspension of 5,6-diamino-1 2 3,4-tetrahydronaphthalene (0.32 g, 2 mmol) in 5 ml of M hydrochloric acid was refluxed with oxalic acid dihydrate (0.38, 3 mmol) for 5 h. After cooling, the precipitate was isolated by filtration, washed with water, ethanol and ether giving 0.31 g (72%) of the title compound; m.p. >300° C.; IR (KBr): 1695 cm-1 (C=0),1H-NMR (DMSO-d6): 1.5-1.9 (m, 4H,2×CH2), 2.5-2.8 (m,4H,2×CH2), 6.63 (d,J=8Hz, 1H, ArH), 6.83 (d,J=8Hz, 1H, ArH), 10.94 (broad s, 1H, 0H), 11.77 (broad s, 1H, 0H)

Workup

  1. temperatureAfter cooling
  2. customthe precipitate was isolated by filtration
  3. washwashed with water, ethanol and ether giving 0.31 g (72%) of the title compound

Sources & evidence

ORD record
ord-ecbe4e7bd91f46d5a5e9a4dfef6061e8
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

Loading…