Oxalic acid dihydrate → HCID 178513484, compound

HRID 477768Notes

Reaction equation

HRID 477768 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH2:10]2)=[C:5]([N+:13]([O-])=O)[C:4]=1[N+:16]([O-])=O)#[N:2].[OH2:19].O.[C:21](O)(=[O:25])[C:22](O)=[O:23]>C(O)C.[Pd]>[C:1]([C:3]1[C:4]2[N:16]=[C:22]([OH:23])[C:21]([OH:25])=[N:13][C:5]=2[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)(=[O:19])[NH2:2]

Participants

5

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 15066366HCID 15066366, compound

Product 1

HCID 178513484HCID 178513484, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7-cyano-1,2,3,4-tetrahydro-5,6-dinitro-naphthalene (0.18 g, 0.73 mmol) in ethanol was hydrogenated at room temperature and atmospheric pressure in the presence of 100 mg of 5% palladium-on-charcoal. The catalyst was filtered off, and the filtrate was evaporated to dryness. The solid residue was suspended in 10 ml of 1M hydrochloric acid, oxalic acid dihydrate (0.15 g, 1.2 mmol) was added, and the mixture was refluxed for 3 h. After cooling, the solid was collected and washed with water, ethanol and ether affording 80 mg (42%) of the amide.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated to dryness
  4. temperaturethe mixture was refluxed for 3 h
  5. temperatureAfter cooling
  6. customthe solid was collected
  7. washwashed with water, ethanol and ether affording 80 mg (42%) of the amide

Sources & evidence

ORD record
ord-0180999db6264b4ba6caae35547e36b2
Source dataset
uspto-grants-1989_12
Patent number
US04889855

Reaction notes

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