Ammonium Chloride → 7-Amino-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1725937Notes

Reaction equation

HRID 1725937 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 384457-Nitro-1-tetralone

Product 1

HCID 3271777-Amino-1,2,3,4-tetrahydronaphthalen-1-oneYield 89.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 7-nitro-3,4-dihydro-1(2H)-naphthalenone (10.0 g, 52.3 mmol) in ethanol/water (4:1 mixture, 200 mL) was treated with iron (10.3 g), and ammonium chloride (1.1 g), stirred at 85° C. for 4 hours, and filtered. The filtrate was concentrated and the concentrate was dissolved in 400 mL of ethyl acetate, washed with brine (5×), dried (Na2SO4), filtered, and concentrated. The concentrate was treated with diethyl ether and filtered. The filter cake was washed with diethyl ether and dried under vacuum to provide 7.56 g of the desired product. The filtrate was concentrated to provide 0.39 g of additional product. MS (DCI) m/e 162 (M+H)+, 179 (M+NH4)+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutionthe concentrate was dissolved in 400 mL of ethyl acetate
  4. washwashed with brine (5×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. additionThe concentrate was treated with diethyl ether
  9. filtrationfiltered
  10. washThe filter cake was washed with diethyl ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-de1212d22bee4b648c9d7b7ed4e6ddb7
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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