Ethylamine → HCID 21937437, compound

HRID 2121967Notes

Reaction equation

HRID 2121967 reaction equation
F[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([NH2:14])[CH3:13]>C1COCC1.CCOC(C)=O>[CH2:12]([NH:14][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[CH3:13]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 21937437HCID 21937437, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a pressure tube was added 4-fluoro-3-nitroaniline (550 mg, 3.50 mmol) and a 2.0 M solution of ethylamine in THF (8 mL). The sealed tube was heated at 120° C. for 24 h. The reaction solution was cooled, diluted with EtOAc (30 mL), washed with satd NaHCO3 (2×25 mL), dried over Na2SO4, and concentrated under reduced pressure to provide the title compound (625 mg, 98%) as a purple solid. 1H-NMR (CDCl3): δ 7.72 (1H, br s), 7.49 (1H, d), 6.96 (1H, dd), 6.74 (1H, d), 3.45 (2H, br s), 3.30 (2H, m), 1.33 (3H, t).

Workup

  1. temperatureThe reaction solution was cooled
  2. washwashed with satd NaHCO3 (2×25 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23fa9a3ffc2c43ea920b2b2f6e4738ff
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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