Hydroxylamine → HCID 72956735, compound

HRID 1372163Notes

Reaction equation

HRID 1372163 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:17]=O)[C:11]3[O:15][CH:14]=[CH:13][C:12]=3[CH:16]=2)=[CH:4][CH:3]=1.[NH2:19][OH:20].CO.N1C=CC=CC=1>CCOCC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:17]=[N:19][OH:20])[C:11]3[O:15][CH:14]=[CH:13][C:12]=3[CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 887MethanolHCID 1049PyridineHCID 21071788HCID 21071788, compound

Product 1

HCID 72956735HCID 72956735, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
68 °C

Procedure

To a 10 ml round bottom flask was added 5-(4-hydroxyphenyl)-benzofuran-7-carbaldehyde (76 mg, 0.32 mmol), hydroxylamine hydrochlorode (44.4 mg, 0.64 mmol), anhydrous MeOH (2 ml), and anhydrous pyridine (0.06 ml, 0.67 mmol). The reaction was then heated to 68° C. and the reaction was done in 5 minutes. The reaction was then 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 20 mg (25%) of product as a yellow solid: 1H NMR (300 MHz, DMSO-d6): δ 6.86 (2H, d, J=8.5 Hz), 7.03 (1H, d, J=2.1 Hz), 7.51 (2H, d, J=8.5 Hz), 7.73 (1H, d, J=1.4 Hz), 7.84 (1H, d, J=1.6 Hz), 8.08 (1H, d, J=2.1 Hz), 8.45 (1H, s) 9.56 (1H, s), 11.57 (1H, s); MS (ESI) m/z 254 ([M+H]+).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customthe layers separated
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated to 20 mg (25%) of product as a yellow solid

Sources & evidence

ORD record
ord-4d6ae22da3a1480cbfcd9e389d03adc5
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

Loading…