Hydrochloric Acid → BenzeneMethanaMine, N-hydroxy-4-Methoxy-, hydrochloride

HRID 521702Notes

Reaction equation

HRID 521702 reaction equation
C(=O)([O-])OC(C)(C)C[N:5](C(OC(C)(C)C)=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[ClH:26].[O:27]1CCOCC1>>[ClH:26].[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][NH:5][OH:27])=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131735501HCID 131735501, compound

Product 1

HCID 14157468BenzeneMethanaMine, N-hydroxy-4-Methoxy-, hydrochloride

Procedure

[tert-Butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]tert-butyl carbonate (1.125 Kg, 3.1 mol) is dissolved in 1,4-dioxane (2.8 L) and a hydrogen chloride solution (4 M in dioxane, 3.15 L, 12.4 mol) is added drop wise over 1 hour 30 minutes. The solution is stirred at room temperature overnight. The title product is collected by filtration as white solid (488.0 g, 81%). 1H NMR (d6-DMSO) δ 11.71 (s, 2H), 10.94 (s, 1H), 7.44 (d, J=8.8 Hz, 2H), 6.95 (d, J=8.8 Hz, 2H), 4.22 (s, 2H), 3.75 (s, 3H).

Workup

  1. filtrationThe title product is collected by filtration as white solid (488.0 g, 81%)

Sources & evidence

ORD record
ord-e875c848e84e4deaa8ba30b0dbb70f95
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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