Ethanolamine → Methyl 4-[(2-hydroxyethyl)amino]-3-nitrobenzoate

HRID 555271Notes

Reaction equation

HRID 555271 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](F)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.CCN(C(C)C)C(C)C.[NH2:24][CH2:25][CH2:26][OH:27]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:24][CH2:25][CH2:26][OH:27])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 12257330Methyl 4-[(2-hydroxyethyl)amino]-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluoro-3-nitro-benzoic acid methyl ester (3 g, 15.64 mmol) was dissolved in DMF (20 ml) and DIPEA (5.8 g, 18.07 mmol) was added. 2-Aminoethanol (1.1 g, 18.07 mmol) was then added slowly by maintaining the temperature <20° C. Stirring continued at ambient temperature for 1 h. After checking the completion of reaction by TLC, the reaction mixture was added onto the ice cold water. The yellow solid which separated out was filtered, washed with cold water and finally washed with hexane affording 3.3 g (92%) of 4-(2-hydroxyethylamino)-3-nitro-benzoic acid methyl ester. 1H NMR (300 MHz, CDCl3) δ 3.5 (q, 2H), 3.7 (q, 2H), 3.9 (s, 3H), 5.1 (t, 1H), 7.2 (d, 1H), 8.0 (d, 1H), 8.6 (s, 1H).

Workup

  1. temperatureby maintaining the temperature <20° C
  2. customthe completion of reaction by TLC
  3. customThe yellow solid which separated out
  4. filtrationwas filtered
  5. washwashed with cold water
  6. washfinally washed with hexane affording 3.3 g (92%) of 4-(2-hydroxyethylamino)-3-nitro-benzoic acid methyl ester

Sources & evidence

ORD record
ord-0fcd14e571b64774845171a56d73c11b
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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