O-ethylhydroxylamine hydrochloride → HCID 86757976, compound

HRID 843176Notes

Reaction equation

HRID 843176 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:23])[CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:24]=O.Cl.[CH2:27]([O:29][NH2:30])[CH3:28]>N1C=CC=CC=1>[CH2:27]([O:29][N:30]=[CH:24][C:3]1[O:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:23])[CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[C:2]=1[CH3:1])[CH3:28]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 22614941HCID 22614941, compound

Product 1

HCID 86757976HCID 86757976, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-methyl-4-[3-(methyl-pyridin-3-ylmethyl-amino)-propoxy]-benzofuran-2-carbaldehyde (the compound of Example 115-b) (29 mg) in pyridine (5 ml) was added O-ethyl hydroxylamine hydrochloride (84 mg) at room temperature. After stirring for seven hours, the mixture was partitioned between ethyl acetate and NH4Cl solution. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography developed by dichloromethane and methanol to give the title compound as a colorless oil (19 mg). ESI-MS: m/z 382 (MH+); 1H-NMR (CDCl3): δ 1.35 (3H, t, J=6.9 Hz), 2.03 (2H, m), 2.27 (3H, s), 2.29 (3H, s), 2.59 (2H, t, J=6.9 Hz), 3.52 (2H, s), 4.11 (2H, t, J=5.9 Hz), 4.32 (2H, q, J=6.9 Hz), 6.60 (1H, d, J=7.6 Hz), 7.05-7.11 (2H, m), 7.21 (1H, t, J=7.9 Hz), 7.58-7.63 (1H, m), 8.12 (1H, s), 8.42 (1H, dd, J=1.7 Hz, 4.9 Hz), 8.52 (1H, d, J=2.0 Hz).

Workup

  1. customthe mixture was partitioned between ethyl acetate and NH4Cl solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3da2acd18d8447b3adc6ee225e422a2a
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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