Aniline → HCID 13564463、化合物

HRID 1284558ノート

反応式

HRID 1284558 の反応式
[OH:1][C:2]1[C:11]([CH:12]=O)=[C:6]2[CH2:7][CH2:8][CH2:9][O:10][C:5]2=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:11]=1[CH2:12][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

4

反応物 2

HCID 6115AnilineHCID 13564460HCID 13564460、化合物

生成物 1

HCID 13564463HCID 13564463、化合物収率 26%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of 6-hydroxy-dihydrobenzopyran- 5-carboxaldehyde (206 mg, 1.16 mmol) and aniline (108 mg, 1.16 mmol) in benzene (6 mL) was heated to reflux for 30 minutes under nitrogen. After cooling the mixture was passed through a short column of silica gel and the eluate concentrated to an orange solid (119 mg). This material was taken up in methanol (10 mL) and hydrogenated at 40 psi using 10% Pd/C (12 mg) as catalyst. After filtration and concentration the crude product was purified by chromatography over silica gel (Hexane/ethyl acetate, 85/15, an eluant) to afford 6-hydroxy-5-phenylaminomethyl-3,4-dihydrobenzopyran (77 mg, 26%) m.p. 105°-107° C.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes under nitrogen
  3. temperatureAfter cooling the mixture
  4. concentrationthe eluate concentrated to an orange solid (119 mg)
  5. filtrationAfter filtration and concentration the crude product
  6. customwas purified by chromatography over silica gel (Hexane/ethyl acetate, 85/15

出典と根拠

ORDレコード
ord-4505a02798f64811a3b783566df71e39
出典データセット
uspto-grants-1986_01
特許番号
US04563476

反応ノート

読み込み中…