HCID 13318640, compound → HCID 13318627, compound

HRID 544341Notes

Reaction equation

HRID 544341 reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH:14]([N:19]=[N+]=[N-])[CH2:13][CH2:12][C:11]=2[C:10]=1[C:22]([NH2:24])=[O:23])C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH:14]([NH2:19])[CH2:13][CH2:12][C:11]=2[C:10]=1[C:22]([NH2:24])=[O:23]

Participants

4

Reactant 1

HCID 13318640HCID 13318640, compound

Product 1

HCID 13318627HCID 13318627, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution was prepared by dissolving 0.7 g. of dl-2-benzyloxy-6-azido-5,6,7,8-tetrahydro-1-naphthalenecarboxamide in 50 ml. of ethanol. The solution was placed in a low pressure hydrogenation apparatus and hydrogenated over a palladium-on-carbon catalyst at about 60 psi. After the theoretical quantity of hydrogen had been absorbed, the hydrogenation mixture was removed from the apparatus and the catalyst separated by filtration. Evaporation of the solvent from the filtrate yielded dl-2-hydroxy-6-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxamide. The residue was dissolved in methanol and gaseous hydrogen chloride passed into the methanol solution, thus forming the hydrochloride salt. Ether was added to the solution to the point of incipient precipitation and the solution was cooled. Crystalline dl-2-hydroxy-6-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxamide hydrochloride thus obtained melted at 245° C.; yield=0.3 g.

Workup

  1. customA solution was prepared
  2. dissolutionby dissolving 0.7 g
  3. customAfter the theoretical quantity of hydrogen had been absorbed
  4. customthe hydrogenation mixture was removed from the apparatus
  5. customthe catalyst separated by filtration
  6. customEvaporation of the solvent from the filtrate

Sources & evidence

ORD record
ord-f349416c0d954294b7bf043ed36cc6ff
Source dataset
uspto-grants-1984_05
Patent number
US04448990

Reaction notes

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