Methylamine → HCID 21930417, compound

HRID 1243691Notes

Reaction equation

HRID 1243691 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[OH:19])[CH:3]=1.CN.[C:22]([BH3-])#[N:23].[Na+].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30]>C(OCC)(=O)C.C(O)(=O)C.CO>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[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:23][CH3:22])[C:12]=2[OH:19])[CH:3]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 21930371HCID 21930371, compound

Product 1

HCID 21930417HCID 21930417, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10129899Acetic acid methanolSolvent

Procedure

4-Chloro-2-(3-formyl-2-hydroxyphenoxy)-benzonitrile (0.30 g, 1.10 mmol), methylamine (2M in methanol, 2.5 mL, 5.0 mmol) and sodium cyanoborohydride (0.10 g, 1.6 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (35 mL) for 19 h. The solvent was removed in vacuo. The residue was treated with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. To the ethyl acetate layer was added fumaric acid (0.12 g, 1.03 mmol) and the solvent removed in vacuo. The residue was triturated with ethyl acetate overnight, collected by filtration, and dried to give 4-chloro-2-[2-hydroxy-3-(methylaminomethyl)phenoxy]-benzonitrile fumarate (256 mg, 58%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with saturated sodium hydrogen carbonate solution
  3. extractionextracted with ethyl acetate
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with ethyl acetate overnight
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-87a5be889456446287e346018bb425c1
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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