Ammonia → HCID 18968908, compound

HRID 398790Notes

Reaction equation

HRID 398790 reaction equation
Cl.[NH2:2][CH:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][C:13]3[C:18]([C:6]=2[CH2:5][CH2:4]1)=[CH:17][CH:16]=[CH:15][CH:14]=3.N>O>[NH2:2][CH:3]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][C:13]3[C:18]([C:6]=2[CH2:5][CH2:4]1)=[CH:17][CH:16]=[CH:15][CH:14]=3

Participants

4

Reactant 2

HCID 222AmmoniaHCID 18968915HCID 18968915, compound

Product 1

HCID 18968908HCID 18968908, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-azido-4-oxo-2,3,4,5-tetrahydro-1H-naphtho-[2,1-b]azepine (16.0 g, 63.4 mmol) in a mixture of dry dioxane (150 ml) and ethanol (150 ml), palladium on carbon (10%, 2 g) was added. This mixture was hydrogenated under a pressure of 5 bar and with efficient stirring for 24 h. The reaction mixture was filtered and excess hydrogenchloride in ethanol was added. The precipitated solid was isolated, washed with ethanol and dried to give 14.4 g of 3-amino-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine hydrochloride. The above hydrochloride (14.2 g) was dissolved into water (800 ml) by warming. A 25% aqueous ammonia solution was added and a precipitate was formed. The solid was isolated by filtration, washed with water and dried in vacuo to give 11.9 g of 3-amino-4-oxo-2,3,4,5-tetrahydro-1H-naphtho[2,1-b]azepine.

Workup

  1. temperatureby warming
  2. customa precipitate was formed
  3. customThe solid was isolated by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e1b24c1230fa4921b11737de325bd374
Source dataset
uspto-grants-1998_10
Patent number
US05817654

Reaction notes

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