Sodium cyanoborohydride → HCID 21947495, compound

HRID 2214584Notes

Reaction equation

HRID 2214584 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11].C([BH3-])#N.[Na+]>>[CH3:1][O:2][NH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11]

Participants

3

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 54237564HCID 54237564, compound

Product 1

HCID 21947495HCID 21947495, compoundYield 83%

Procedure

Reduction of 2-methylbenzaldehyde O-methyloxime with sodium cyanoborohydride as described in the preparation of Compound 44-B gave the title hydroxylamine as a clear oil (83% yield). 1HNMR 400 MHz (CDCl3) δ (ppm): 2.42 (3H, s, CH3), 3.55 (3H, s, OCH3), 4.11 (2H, s, NCH2), 5.64 (1H, s, NH), 7.19–7.32 (4H, m, aromatics). The hydrochloride salt was obtained as a white solid: mp 148–150° C. Anal. calcd. for C9H13NO—HCl: C, 57.60; H, 7.51; N, 7.46. Found: C, 57.59; H, 7.69; N, 7.52.

Sources & evidence

ORD record
ord-e4692d42d0ef4fd59076033dc2ac8811
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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