Hydrochloric Acid → 7-nitro-1,2,3,4-tetrahydro-1-naphthalenamine

HRID 2288063Notes

Reaction equation

HRID 2288063 reaction equation
C([O-])(=O)C.[NH4+].[C:6]([BH3-])#[N:7].[Na+].[N+:10]([C:13]1[CH:22]=[C:21]2[C:16]([CH2:17][CH2:18][CH2:19]C2=O)=[CH:15][CH:14]=1)([O-:12])=[O:11].Cl>CO>[N+:10]([C:13]1[CH:22]=[C:21]2[C:16]([CH2:17][CH2:18][CH2:19][CH:6]2[NH2:7])=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 384457-Nitro-1-tetraloneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 121368527-nitro-1,2,3,4-tetrahydro-1-naphthalenamineYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

24 g (314 mmol) of ammonium acetate and 13.8 g (220 mmol) of sodium cyanoborohydride were added to a solution of 6.0 g (31 mmol) of 7-nitro-3,4-dihydro-2H-naphthalen-1-one in 150 ml of methanol, and the reaction mixture was heated at 60° C. for 3 h. After acidifying to pH<2 with dil. hydrochloric acid, the reaction mixture was concentrated in vacuo and the residue was stirred with water and EA. A precipitate which appeared here was filtered off with suction, washed with EA and then combined with the acidic aqueous phase. After rendering the mixture alkaline, it was extracted with EA and the organic phase was dried with magnesium sulfate and concentrated in vacuo. 3.6 g of 7-nitro-1,2,3,4-tetrahydro-1-naphthylamine were obtained.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. filtrationA precipitate which appeared here was filtered off with suction
  3. washwashed with EA
  4. extractionwas extracted with EA
  5. dry with materialthe organic phase was dried with magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4b945b4d4bc441387c9777ddb74cada
Source dataset
uspto-grants-2000_07
Patent number
US06087399

Reaction notes

Loading…