Aniline → HCID 13564463, compound

HRID 1284558Notes

Reaction equation

HRID 1284558 reaction equation
[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

Participants

4

Reactant 2

HCID 6115AnilineHCID 13564460HCID 13564460, compound

Product 1

HCID 13564463HCID 13564463, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4505a02798f64811a3b783566df71e39
Source dataset
uspto-grants-1986_01
Patent number
US04563476

Reaction notes

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