Methylamine → HCID 86595618, compound

HRID 1178517Notes

Reaction equation

HRID 1178517 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.CN.[C:24]([BH3-])#[N:25].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(O)(=O)C.CO>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[CH3:1][O:2][C:3]1[C:10]([O:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][CH2:24][NH2:25]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 21930390HCID 21930390, compound

Product 1

HCID 86595618HCID 86595618, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

2-Methoxy-3-(5-methyl-2-nitrophenoxy)benzaldehyde (0.36 g, 1.3 mmol), methylamine (2M in methanol, 3.0 mL, 6.0 mmol) and sodium cyanoborohydride (100 mg, 1.6 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (50 mL) for 18 h. The solvent was removed in vacuo. The residue was treated with 10% sodium carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was separated and fumaric acid (0.14 g, 1.2 mmol) was added. After the solvent was removed in vacuo, the residue was triturated with hot methanol and allowed to cool overnight. The filtrate was collected, the solvent removed in vacuo. The residue was triturated with ethyl acetate overnight, collected by filtration, and dried to give [2-methoxy-3-(5-methyl-2-nitrophenoxy)benzyl]methylamine fumarate (195 mg, 38%) as a beige solid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with 10% sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate layer was separated
  5. customAfter the solvent was removed in vacuo
  6. customthe residue was triturated with hot methanol
  7. temperatureto cool overnight
  8. customThe filtrate was collected
  9. customthe solvent removed in vacuo
  10. customThe residue was triturated with ethyl acetate overnight
  11. filtrationcollected by filtration
  12. customdried

Sources & evidence

ORD record
ord-aaaa06819c2143e59039b3f5f378d46e
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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