Methanol → HCID 86597104, compound

HRID 1297274Notes

Reaction equation

HRID 1297274 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]=O)=[C:16]2[CH3:26])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:28][OH:29].CO>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]=[N:28][OH:29])=[C:16]2[CH3:26])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 86034609HCID 86034609, compound

Product 1

HCID 86597104HCID 86597104, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(4-benzyloxyphenyl)-2-methyl-1H-indole-3-carbaldehyde (0.64 g, 1.9 mmol), hydroxylamine hydrochloride (0.25 g, 3.6 mmol), methanol (25 mL) and pyridine (1 mL) was heated to reflux for 30 min. The mixture was cooled, the methanol removed by evaporation. The product was extracted into ethyl acetate (2×50 mL) and the organic layer was washed with water and brine and dried over MgSO4. The solvent was evaporated, and the product was purified by silica gel chromatography (25% ethyl acetate-hexanes) to provide a white solid (53%): mp 171-173° C.; 1H NMR (DMSO-d6): δ 2.31 (3H, s), 5.20 (2H, s), 6.94-7. J01 (1H, m), 7.10-7.14 (2H, m), 7.23 (2H, d, J=8.9 Hz), 7.37-7.47 (5H, m), 7.52 (2H, d, J=7.4 Hz), 8.01-8.03 (1H, m), 8.41 (1 H, s), 10.66 (1H, s); MS m/z (M+H)+357. Anal. for C23H20N2O2·0.5H2O: Calc'd: C, 75.60; H, 5.79; N, 7.67. Found: C, 75.12; H, 5.53; N, 7.34.

Workup

  1. temperatureto reflux for 30 min
  2. temperatureThe mixture was cooled
  3. customthe methanol removed by evaporation
  4. extractionThe product was extracted into ethyl acetate (2×50 mL)
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated
  8. customthe product was purified by silica gel chromatography (25% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-12d388906bbb4a0bb18ab98869b699df
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

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