Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 57758083, compound

HRID 250724Notes

Reaction equation

HRID 250724 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].Cl.[CH3:15][NH:16][O:17][CH3:18].Cl.CN(C)CCCN=C=NCC.C(N(C1C=CC=CN=1)CC)C>ClCCl>[CH3:15][N:16]([O:17][CH3:18])[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2306533-Fluoro-4-nitrobenzoic acidHCID 232542N,N-Diethylpyridin-2-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57758083HCID 57758083, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-Fluoro-4-nitro-benzoic acid (10.7 g, 57.71 mmol) in 1000 mL anhydrous dichloromethane. Add N,O-Dimethylhydroxylamine hydrochloride (4.5 g, 46.17 mmol), followed by 1-(3 dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (16.60 g, 86.57 mmol) and 4 diethylaminopyridine (6.77 g, 55.4 mmol). Stir at room temperature under nitrogen atmosphere overnight. Concentrate under reduced pressure and partition the residue between ethyl acetate (300 mL) and water (100 mL). Wash the organic layer with saturated aqueous sodium chloride (4×30 mL) and dry over magnesium sulfate. Concentrate under reduced pressure to provide the desired compound (7.4 g, 56%).

Workup

  1. concentrationConcentrate under reduced pressure
  2. custompartition the residue between ethyl acetate (300 mL) and water (100 mL)
  3. washWash the organic layer with saturated aqueous sodium chloride (4×30 mL)
  4. dry with materialdry over magnesium sulfate
  5. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-ea61d4d7423a41729e99a2e3da681c3a
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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