Ammonia → HCID 17827987, compound

HRID 635630Notes

Reaction equation

HRID 635630 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=[N:14]O)[CH2:12][CH3:13].C([O-])(=O)C.[NH4+].N.[OH-].[Na+]>C(OCC)C.[Zn].CN(C)C=O.C(O)C>[CH2:12]([CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[NH2:14])[CH3:13]

Participants

9

Reactant 4

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 862061451-(2-Naphthalenyl)-1-propanone oxime

Product 1

HCID 17827987HCID 17827987, compoundYield 97.2%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of2 g (10 mmol) of 1-(2-naphthyl)-1-propanone oxime, 3.6 g (55.1 mmol) of zinc, 0.4 g (6 mmol) of ammonium acetate, 50 ml of aqueous ammonia, 12 ml of ethanol and 5 ml of dimethylformamide was stirred and heated at 85° C. for 1 hour. The mixture was cooled to room temperature, diluted with diethyl ether and basified with 35% aqueous sodium hydroxide solution. The ethereal layer was separated, dried over magnesium sulphate, filtered and evaporated to dryness to give 1.8 g of α(RS)-ethyl-2-naphthalenemethylamine as a colorless oil, 1H NMR (400 MHz, CDCL3) δ: 0.9 (t,3H), 1.7-1.8 (br,s,2H), 3.9-4.0 (t,1H), 4.1-4.2 (q,2H), 7.4-7.5 (m,3H), 7.75 (s,1H), 7.8-7.9 (m,3H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe ethereal layer was separated
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9d8639e484e44615a770138701f66c36
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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