Hydroxylamine → HCID 178472252, compound

HRID 1664195Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][C:7]#[N:8].[NH2:9][OH:10].[C:11]([C:18]([O:20][CH2:21][CH3:22])=[O:19])#[C:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][C:7](=[NH:8])[NH:9][O:10][C:11](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

Reactant 3

HCID 787Hydroxylamine

HCID 69803Diethyl acetylenedicarboxylate

HCID 904513-(2-Hydroxyethoxy)propiononitrile

Product 1

HCID 178472252HCID 178472252, compoundYield 86.6%

Procedure

Treatment of 3-(2-hydroxyethoxy)propanenitrile (9.00 g, 78.1 mmol) with 50% aqueous hydroxylamine (5.16 g, 78.1 mmol) followed by reaction with diethyl acetylenedicarboxylate (13.30 g, 78.1 mmol) gave 21.53 g (86% yield) of the title material as a light yellow oil after chromatography. 1HNMR 400 MHz (CDCl3) δ (ppm): (mixture of E/Z isomers ratio˜3:1) 1.25-1.4 (6H, 4×t), 2.42-2.49 (2H, m), 3.60-3.79 (6H, m), 4.16-4.21 (2H, m), 4.33-4.38 (2H, m), 5.3 and 5.65 (2H, two broad s), 5.77 and 5.83 (1H, 2×s). MS (ESI+) m/e 319 [M+H+].

Sources & evidence

ORD record: ord-52908c286efe4be0aa19f6cbf63b0453
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039458B2

Reaction notes

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