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

HRID 555271노트

반응식

HRID 555271 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0fcd14e571b64774845171a56d73c11b
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053431B2

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