Aniline → HCID 13564463, 화합물

HRID 1284558노트

반응식

HRID 1284558 반응식
[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

참가 물질

4

반응물 2

HCID 6115AnilineHCID 13564460HCID 13564460, 화합물

생성물 1

HCID 13564463HCID 13564463, 화합물수율 26%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4505a02798f64811a3b783566df71e39
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04563476

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