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

HRID 555271ノート

反応式

HRID 555271 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0fcd14e571b64774845171a56d73c11b
出典データセット
uspto-grants-2011_11
特許番号
US08053431B2

反応ノート

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