4-Methylmorpholine → HCID 86649965, compound

HRID 1042480Notes

Reaction equation

HRID 1042480 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH3:18][O:17][N:16]([CH3:15])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[N+:11]([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27374164-Fluoro-2-nitrobenzoic acid

Product 1

HCID 86649965HCID 86649965, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-2-nitrobenzoic acid (1 g, 5.4 mmol), N,O-dimethylhydroxylamine hydrochloride (0.58 g, 5.95 mmol) and N-methylmorpholine (0.65 mL, 5.91 mmol) in dichloromethane (20 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.14 g, 5.95 mmol). The mixture was stirred for 80 minutes at room temperature. The mixture was concentrated under reduced pressure and then diluted with EtOAc and water. The organic layer was washed with 3 N HCl, saturated aqueous NaHCO3 solution and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give N-methoxy-N-methyl-4-fluoro-2-nitro-benzamide (1.15 g, 95%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with EtOAc and water
  3. washThe organic layer was washed with 3 N HCl, saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cfb4bd4866e4587aed97927252c575a
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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