4-Methylmorpholine → HCID 57758083, compound

HRID 229625Notes

Reaction equation

HRID 229625 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].CCN=C=NCCCN(C)C.CN1CCOCC1.Cl.[CH3:33][O:34][NH:35][CH3:36]>Cl.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([N:35]([O:34][CH3:33])[CH3:36])=[O:6]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 57758083HCID 57758083, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of CH2Cl2 (1L) was added 3-fluoro-4-nitrobenzoic acid (100 g, 540 mmol) and EDCI (155.3 g, 810 mmol) followed by NMM (178 mL, 1.62 mol) and N-methoxymethanamine hydrochloride (79.0 g, 810 mmol). The solution was allowed to stir under N2 at rt for 17 h. The reaction mixture was then diluted with 1N HCl (1 L), transferred to separatory funnel, and separated. The organic phase was washed with 1N NaOH (2×500 mL) and water (250 ML). All aqueous layers were back extracted with EtOAc (2×500 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated in vacuo. to afford 102.3 g of the above compound as a yellow solid (448 mmol, yield 83%). 1H-NMR (DMSO-d6) δ 8.22 to 8.18 (t, J=8.0 Hz, 1H), 7.79 to 7.76 (d, J=11.5 Hz, 1H), 7.60 to 7.58 (d, J=8.3 Hz, 1H), 3.56 (s, 3H), 3.28 (s, 3H); MS [M+H]+=229. 1; LCMS RT=2.27 min.

Workup

  1. customtransferred to separatory funnel
  2. customseparated
  3. washThe organic phase was washed with 1N NaOH (2×500 mL) and water (250 ML)
  4. extractionAll aqueous layers were back extracted with EtOAc (2×500 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82bcedf80a6e4c2983713ab5b0a14db7
Source dataset
uspto-grants-2009_07
Patent number
US07563791B2

Reaction notes

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