Ethanolamine → HCID 59515678, compound

HRID 1161187Notes

Reaction equation

HRID 1161187 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[CH2:15]([CH2:17][NH2:18])[OH:16].C(N(CC)CC)C>CO>[OH:16][CH2:15][CH2:17][N:18]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:9]1=[O:14]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 59515678HCID 59515678, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

5-nitro-isochromen-1-one (3.60 g, 0.0170 mol) was suspended in methanol (40 mL), ethanolamine (3.11 g, 0.0508 mol) was added and the reaction mixture was stirred at 70° C. for 2 h under an atmosphere of nitrogen. The mixture was cooled to room temperature and triethylamine (5 mL) was added and the reaction mixture was stirred at room temperature for 2 days. The resulting solid was filtered out (yellow solid was obtained as the desired product, 0.9 g). The filtrate was concentrated and the residue was dissolved in ethylacetate, washed by water and brine, dried over sodium sulfate. Solvent was removed to obtain product as yellow solid (1.3 g). MS m/z=235.1 (M+1).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringthe reaction mixture was stirred at room temperature for 2 days
  3. filtrationThe resulting solid was filtered out (yellow solid

Sources & evidence

ORD record
ord-56e928ac65ad4bd789a3b22455ccc3cb
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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