Methanol → HCID 72996366, compound

HRID 1297278Notes

Reaction equation

HRID 1297278 reaction equation
[Cl: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]([OH:17])=[CH:13][CH:12]=1)[C:6]([CH3:18])=[C:5]2[CH:19]=O.Cl.[NH2:22][OH:23].CO>N1C=CC=CC=1>[Cl: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]([OH:17])=[CH:13][CH:12]=1)[C:6]([CH3:18])=[C:5]2[CH:19]=[N:22][OH:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 86034612HCID 86034612, compound

Product 1

HCID 72996366HCID 72996366, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-chloro-1-(4-hydroxyphenyl)-2-methyl-1H-indole-3-carbaldehyde (0.63 g, 2.2 mmol), hydroxylamine hydrochloride (0.30 g, 4.3 mmol), methanol (25 mL) and pyridine (1 mL) was reacted according to the procedure used in Example 4 to afford a white solid (68%): mp 212-213° C.; 1H NMR (DMSO-d6): δ 2.29 (3H, s), 6.96 (3H, d, J=8.7 Hz), 7.12 (1H, dd, J=2.2 Hz, J=8.7 Hz), 7.24 (2H, d, J=8.7 Hz), 8.03 (1H, d, J=2.1 Hz), 8.40 (1H, s), 9.93 (1H, s), 10.75 (1H, s); MS m/Z (M+H)+ 301/303 (1 Cl). Anal. for C16H13ClN2O2: Calc'd: C, 63.90; H, 4.36 N, 9.31. Found: C, 63.63; H, 4.12; N, 9.17.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-9d5741ada8da486f984bec15207cd4d4
Source dataset
uspto-grants-2007_07
Patent number
US07250440B2

Reaction notes

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