Ammonium Acetate → HCID 58368683, compound

HRID 1192548Notes

Reaction equation

HRID 1192548 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:4]([C:19](=O)[CH3:20])[CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:4]([CH:19]([NH2:28])[CH3:20])[CH:3]=1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368651HCID 58368651, compound

Product 1

HCID 58368683HCID 58368683, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[4-chloro-1-(3-fluorophenyl)-2-naphthyl]ethanone (58 mg, 0.19 mmol) and ammonium acetate (150 mg, 1.94 mmol) in methanol (1.1 mL) and acetonitrile (1.1 mL) was heated at 65° C., in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (24.4 mg, 0.388 mmol) was added to the resulting mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with sat. sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The crude material was used directly in the next step (58 mg, 100%). LCMS calculated for C18H13ClF (M−NH2)+: m/z=283.1; Found: 283.0.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. for another 4 hours
  3. temperaturecooled to room temperature
  4. customquenched with sat. sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-6a5b9e803e644521a955cad01d9271f9
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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