3,4-Dichlorobenzaldehyde → N-(3,4-dichloro-benzyl)-O-methyl-hydroxylamine

HRID 2214546Notes

Reaction equation

HRID 2214546 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.Cl.[O:12]([NH2:14])[CH3:13].C([BH3-])#N.[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH:14][O:12][CH3:13]

Participants

4

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 521874O-Methylhydroxylamine hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 12147061N-(3,4-dichloro-benzyl)-O-methyl-hydroxylamine

Procedure

Reaction of 3,4-dichlorobenzaldehyde with methoxylamine hydrochloride followed by reduction with sodium cyanoborohydride as described in the preparation of Compound 44-A and 44-B gave the title hydroxylamine as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.48 (3H, s), 3.99 (2H, s), 5.74 (1H, broad s), 7.20 (1H, dd, J=2.0 Hz and J=8.1 Hz), 7.40 (1H, d, J=8.1 Hz), 7.47 (1H, d, J=2.0 Hz).

Sources & evidence

ORD record
ord-de4495b3e3ca4da3bedb0e8ff2070be6
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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