Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 57825237, compound

HRID 1668752Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([C:7](N(OC)C)=[O:8])=[CH:5][C:4]=1[CH3:15].COC1C=CC(C(O)=O)=CC=1C.Cl.CNOC.[Br:33][C:34]1[CH:39]=[C:38]([CH2:40][CH2:41][O:42][CH3:43])[CH:37]=[C:36](Br)[CH:35]=1.C([Li])CCC>>[Br:33][C:34]1[CH:35]=[C:36]([C:7]([C:6]2[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[C:4]([CH3:15])[CH:5]=2)=[O:8])[CH:37]=[C:38]([CH2:40][CH2:41][O:42][CH3:43])[CH:39]=1

Participants

Reactant 5

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

HCID 27595834-Methoxy-3-methylbenzoic Acid

HCID 57825114HCID 57825114, compound

HCID 58137697HCID 58137697, compound

HCID 178418339Butyllithium

Product 1

HCID 57825237HCID 57825237, compoundYield 53%

Procedure

In analogy to the procedure described for the preparation of the Building Block AU, the reaction of 4,N-dimethoxy-3,N-dimethyl-benzamide, beforehand prepared by a standard condensation of 4-methoxy-3-methyl-benzoic acid and N,O-dimethylhydroxylamine hydrochloride, and 1,3-dibromo-5-(2-methoxy-ethyl)-benzene, beforehand reacted with n-butyl lithium, yielded the title compound as a colourless oil (yield: 53% of theory). Mass (calculated) C18H19BrO3 [362]; (found) [M+H]+=363, 365.

Workup

customIn analogy to the procedure described for the preparation of the Building Block AU

Sources & evidence

ORD record: ord-1d3f49fb621b426189bb78ff7d0fe204
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989449B2

Reaction notes

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