Hydroxyamine hydrochloride → HCID 178522399, compound

HRID 574678Notes

Reaction equation

[CH:1]([C:3]1[N:8]=[C:7]([OH:9])[C:6]([NH:10][C:11](=[O:25])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][N:4]=1)=O.CC([O-])=O.[Na+].Cl.[OH:32][NH2:33]>O>[OH:9][C:7]1[C:6]([NH:10][C:11](=[O:25])[CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:5][N:4]=[C:3]([CH:1]=[N:33][OH:32])[N:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of compound 3-h (1 g, 3.0 mmol), NaOAc (0.5 g, 6.0 mmol) and hydroxyamine hydrochloride (0.31 g, 4.5 mmol) in H2O (25 mL) was stirred at 100° C. for 2 h. The precipitated was isolated by filtration to afford the product, 3-2-a, as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 12.31 (s, 1H), 9.89 (s, 1H), 8.85 (s, 1H), 7.74 (s, 1H), 7.33-7.23 (m, 1H), 5.71 (s, 1H). LC-MS: (M+H)+ 349.

Workup

customThe precipitated was isolated by filtration
customto afford the product, 3-2-a

Sources & evidence

ORD record: ord-7b5af99a13e04e5e97c71953ec1a05f9
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034851B2

Reaction notes

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