Ammonia → HCID 13318625, compound

HRID 615779Notes

Reaction equation

HRID 615779 reaction equation
O.N.Cl.[OH:4][C:5]1[C:6]([C:16]([NH2:18])=[O:17])=[CH:7][C:8]2[CH2:9][CH:10]([NH2:15])[CH2:11][CH2:12][C:13]=2[CH:14]=1>CO.[Pd]>[OH:4][C:5]1[C:6]([C:16]([NH2:18])=[O:17])=[CH:7][C:8]2[CH2:9][CH:10]([NH2:15])[CH2:11][CH2:12][C:13]=2[CH:14]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 20426672HCID 20426672, compound

Product 1

HCID 13318625HCID 13318625, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent3×

Procedure

A portion of the above free base was converted to the hydrochloride salt. Eight and nine tenths grams of this salt were dissolved in methanol containing 1 ml. of water. Two grams of 5% palladium-on-carbon were added and the mixture hydrogenated at 60 psi. The hydrogenation mixture was then filtered and the filtrate evaporated to dryness in vacuo. A white solid shown by TLC to consist of a single spot comprising methyl dl-3-hydroxy-7-amino-5,6,7,8-tetrahydro-2-naphthoate hydrochloride was obtained. This white solid was dissolved in methanol and the methanol solution cooled to about 0° C. The cooled solution was saturated with gaseous ammonia and the resulting mixture allowed to remain at ambient temperature for about 17 days. At this time, TLC indicated the amidation reaction had gone substantially to completion. The reaction mixture was decolorized with carbon and filtered and the filtrate concentrated in vacuo to yield about 3.5 g. of dl-3-hydroxy-7-amino-5,6,7,8-tetrahydro-2-naphthalenecarboxamide hydrochloride melting at about 300° C.

Workup

  1. filtrationThe hydrogenation mixture was then filtered
  2. customthe filtrate evaporated to dryness in vacuo
  3. customwas obtained
  4. customthe amidation reaction
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto yield about 3.5 g

Sources & evidence

ORD record
ord-f2bc6e24477a4bc1895a4cdec93ea764
Source dataset
uspto-grants-1985_02
Patent number
US04500545

Reaction notes

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