Methanol → HCID 136334157, compound

HRID 1372155Notes

Reaction equation

HRID 1372155 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:17]=O)=[C:12]3[C:16]=2[O:15][CH:14]=[CH:13]3)=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].CO.N1C=CC=CC=1>CCOCC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:17]=[N:20][OH:21])=[C:12]3[C:16]=2[O:15][CH:14]=[CH:13]3)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 21071792HCID 21071792, compound

Product 1

HCID 136334157HCID 136334157, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
68 °C

Procedure

To a 15 ml round bottom flask was added 7-(4-hydroxyphenyl)-benzofuran-4-carbaldehyde (250 mg, 1.05 mmol), hydroxylamine hydrochloride (146 mg, 2.10 mmol), anhydrous MeOH (6.5 ml), and anhydrous pyridine (0.17 ml, 2.10 mmol). The flask was then sealed and heated to 68° C. for 1 h, cooled to room temperature, dilute with ether, and the layers separated. The ether layer was washed with water, dried over anhydrous Na2SO4, passed through a silica plug, and concentrated to 250 mg (94%) clean product as a yellow solid. Further purification was done by chromatography (1:1 EtOAc/hexanes) for analytical analysis: mp 216–217° C.; 1H NMR (300 MHz, DMSO-d6): δ 6.92 (2H, d, J=8.7 Hz), 7.36 (1H, d, J=2.1 Hz), 7.49 (2H, app s), 7.74 (2H, d, J=8.6 Hz), 8.14 (1H, d, J=2.1 Hz), 8.42 (1H, s), 9.73 (1H, s) 11.36 (1H, s); MS (ESI) m/z 254 ([M+H]+).

Workup

  1. customThe flask was then sealed
  2. temperaturecooled to room temperature
  3. customthe layers separated
  4. washThe ether layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated to 250 mg (94%) clean product as a yellow solid
  7. customFurther purification

Sources & evidence

ORD record
ord-bb3c613bfa7745969ecbcf00196d8e91
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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