Ammonium Hydroxide → HCID 118029331, compound

HRID 58208Notes

Reaction equation

HRID 58208 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[NH4+:21].[OH-].CCOC(C)=O.O>C1COCC1>[NH2:21][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 14923Ammonium Hydroxide2×HCID 22728543Water ethylacetateHCID 131736988Tert-butyl (1-(4-fluoro-3-nitrophenyl)ethyl)carbamate

Product 1

HCID 118029331HCID 118029331, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

Tert-butyl (1-(4-fluoro-3-nitrophenyl)ethyl)carbamate (500 g, 1.75 mmol) was stirred in THF (2 ml). NH4OH (0.978 ml, 7.0 mmol) was added and the reaction mixture was heated at 150° C. for 30 minutes using microwave (Biotage Initiator). NH4OH (0.6 00 ml) was added and then heated at 180° C. After cooling to room temperature, the reaction mixture was poured into EtOAc/water. The organic layer was washed with brine, dried over MgSO4 and evaporated. The resulting material was purified by flash chromatography on silica eluting with 0% to 50% EtOAc/Hexane to afford the title compound (376 mg, yield: 76%) 1H-NMR (400 MHz, CDCl3) δ 1.43-1.48 (m, 12H) 4.71 (br. s., 2H) 6.79 (d, 1H) 7.34 (dd, 1H) 8.05 (d, 1H).

Workup

  1. temperatureheated at 180° C
  2. temperatureAfter cooling to room temperature
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe resulting material was purified by flash chromatography on silica eluting with 0% to 50% EtOAc/Hexane

Sources & evidence

ORD record
ord-144665a16c414a9e8f8684acc99b2291
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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