Methylamine → HCID 21930391, compound

HRID 1178466Notes

Reaction equation

HRID 1178466 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=O)[C:12]=2[O:19][CH3:20])[CH:3]=1.CN.[C:23]([BH3-])#[N:24].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>C(OCC)(=O)C.C(O)(=O)C.CO>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][NH:24][CH3:23])[C:12]=2[O:19][CH3:20])[CH:3]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 21930365HCID 21930365, compound

Product 1

HCID 21930391HCID 21930391, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10129899Acetic acid methanolSolvent

Procedure

4-Chloro-2-(3-formyl-2-methoxy-phenoxy)-benzonitrile (0.52 g, 1.8 mmol), methylamine (2M in methanol, 2.7 ml, 5.4 mmol) and sodium cyanoborohydride (0.13 g, 2.1 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (70 ml) for 20 h. The solvent was removed in vacuo. The residue was treated with 10% aqueous sodium carbonate and extracted with ethyl acetate. Fumaric acid (0.21 g, 1.8 mmol) was added to the separated ethyl acetate layer and the solvent removed in vacuo. The residue was triturated with ethyl acetate overnight, filtered and dried to give 4-chloro-2-(2-methoxy-3-methylaminomethyl-phenoxy)-benzonitrile fumarate (583 mg, 77%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with 10% aqueous sodium carbonate
  3. extractionextracted with ethyl acetate
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with ethyl acetate overnight
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-9f719352daaa4091b777b0356235c5d1
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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