Hydrochloric Acid → 4-((Tetrahydropyran-4-yl)amino)-3-nitrobenzoic acid

HRID 74157

反応式

HRID 74157 の反応式
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(N(CC)CC)C.[NH2:21][CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.NC1CCCCO1.Cl>C(O)C.O>[O:25]1[CH2:26][CH2:27][CH:22]([NH:21][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])[CH2:23][CH2:24]1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 8471Triethylamine2 回HCID 679874-Fluoro-3-nitrobenzoic acidHCID 4192234-AminotetrahydropyranHCID 14471248Oxan-2-amine

生成物 1

HCID 436103324-((Tetrahydropyran-4-yl)amino)-3-nitrobenzoic acid収率 101.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

4-Fluoro-3-nitrobenzoic acid (126.4 g, 0.68 mol) was dissolved in ethanol (880 mL). Triethylamine (82.6 g, 0.82 mol), 4-aminotetrahydropyran (82.7 g, 0.81 mol) were added in turn dropwise, and after the additions the reaction solution was heated to reflux. After refluxing for 5 h, triethylamine (8.3 g, 82 mmol), aminotetrahydropyran (8.3 g, 81 mmol) were added, and this was refluxed for a further 9 hours. After the reaction mixture was allowed to cool to room temperature, 2N HCl (880 mL) and water (880 mL) were added and after stirring for awhile, the solid obtained was filtered off. This was forced air-dried at 60° C. to yield the title compound (183.3 g, quant.) as a yellow solid.

後処理

  1. temperatureafter the additions the reaction solution was heated to reflux
  2. temperatureAfter refluxing for 5 h
  3. temperaturethis was refluxed for a further 9 hours
  4. customobtained
  5. filtrationwas filtered off
  6. customThis was forced air-dried at 60° C.

出典と根拠

ORDレコード
ord-3d585bfc7faf417584411f9094ad5215
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

関連ノート

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