Methanol → HCID 86597105, compound

HRID 1297275Notes

Reaction equation

HRID 1297275 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=1)[C:6]([CH3:25])=[C:5]2[CH:26]=O.Cl.[NH2:29][OH:30].CO>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=1)[C:6]([CH3:25])=[C:5]2[CH:26]=[N:29][OH:30]

Participants

5

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 86597102HCID 86597102, compound

Product 1

HCID 86597105HCID 86597105, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-fluoro-1-(4-benzyloxyphenyl)-2-methyl-1H-indole-3-carbaldehyde (0.97 g, 2.7 mmol), hydroxylamine hydrochloride (0.25 g, 3.6 mmol), methanol (25 mL) and pyridine (1 mL) was reacted according to the procedure in Example 3a to afford white solid (88%): mp 183-185° C.; 1H NMR (DMSO-d6): δ 2.30 (3H, s), 5.20 (2H, s) d, 6.94-6.97 (2H, m), 7.23 (2H, d, J=8.9 Hz), 7.37-7.46(5H, m), 7.52(2H, d, J=6.8 Hz), 7.71 (1H, d, J=10.1 Hz), 8.41 (1H, s), 10.72 (1H, s); MS m/z (M+H)+ 375. Anal. for C23H19FN2O2: Calc'd: C, 73.78; H, 5.11 N, 7.48. Found: C, 73.55; H, 5.03; N, 7.35.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-ee9da7a5ff854df0ad1b0c3b6434bf96
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

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