Methylamine → HCID 21930350, compound

HRID 1178463Notes

Reaction equation

HRID 1178463 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][C:14](OC)=[C:13]([CH:19]=O)[CH:12]=2)[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(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]([CH2:19][NH:24][CH3:23])[CH:12]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 21930378HCID 21930378, compound

Product 1

HCID 21930350HCID 21930350, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

4-Chloro-2-(3-formyl-4-methoxy-phenoxy)-benzonitrile (1.00 g, 3.48 mmol), methylamine (2M in methanol, 5.2 ml, 10.4 mmol) and sodium cyanoborohydride (0.24 g, 3.8 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (75 ml) for 18 h. The solvent was removed in vacuo. The residue was treated with 10% aqueous sodium carbonate and extracted with ethyl acetate. The ethyl acetate layer was separated and washed with water, brine and dried over MgSO4. After filtration, fumaric acid (0.40 g, 3.4 mmol) was added to the filtrate and the solvent removed in vacuo. The residue was triturated with ethyl acetate overnight, filtered and dried to give 4-chloro-2-(3-methylaminomethyl-phenoxy)-benzonitrile fumarate (892 mg, 61%) 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 ethyl acetate layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. additionwas added to the filtrate
  8. customthe solvent removed in vacuo
  9. customThe residue was triturated with ethyl acetate overnight
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-be6c3fe4f21143fb9fadf49cb2f76d1a
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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