Ethanolamine → HCID 66965897, compound

HRID 1514917Notes

Reaction equation

HRID 1514917 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13](F)[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[OH:22][CH2:23][CH2:24][NH2:25].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([NH:25][CH2:24][CH2:23][OH:22])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 516892Sodium BicarbonateHCID 62682340HCID 62682340, compound

Product 1

HCID 66965897HCID 66965897, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N-(3,4-dimethyl-phenyl)-3-fluoro-4-nitrobenzamide (65 mg), 2-hydroxy-1-ethylamine (0.225 mL of 2M THF solution) in DMF (1 mL) was heated at 120° C. under microwave radiation for 5 min. Then saturated NaHCO3 aqueous solution was added. The aqueous layer was extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give N-(3,4-dimethyl-phenyl)-3-(2-hydroxy-ethylamino)-4-nitrobenzamide as a yellow oil: MS (m/z) 300 (M+1); 1H NMR (CDCl3, 400 MHz) δ 8.24 (d, 1H), 8.06 (s, 1H), 7.78 (s, 1H), 7.42 (d, 2H), 7.35 (d, 1H), 7.13 (d, 1H), 6.95 (d, 1H), 3.09 (d, 3H), 2.28 (s, 3H), 2.25 (s, 3H), 1.58 (s, 1H).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55cac5df36924a0d8c05948b9073880d
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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