Methylamine → HCID 59203854, compound

HRID 2241805Notes

Reaction equation

HRID 2241805 reaction equation
Cl[C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[OH:17])=[O:7])=[CH:4][N:3]=1.[CH3:20][NH2:21]>CO>[OH:17][C:10]1[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:9]=1[NH:8][C:6](=[O:7])[C:5]1[CH:18]=[CH:19][C:2]([NH:21][CH3:20])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59203847HCID 59203847, compound

Product 1

HCID 59203854HCID 59203854, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
250 °C

Procedure

6-Chloro-N-(2-hydroxy-4-methoxyphenyl)nicotinamide (0.40 g, 1.44 mol) was mixed with a solution of 8M methylamine in methanol (4 mL) and heated in a microwave reactor at 250° C. for 10 minutes. The solvent was evaporated in vacuo and the residue was partitioned between water and ethyl acetate. The aqueous layer was extracted five timed with ethyl acetate The pooled organics were dried (MgSO4), filtered and evaporated. The solid was titurated with CH2Cl2, filtered and dried, giving the title compound (0.25 g) as a solid. 1H NMR δ ppm 9.73 (s, 1H) 9.38 (s, 1H) 8.65 (d, 1H) 7.92 (dd, 1H) 7.33 (d, 1H) 7.16 (d, 1H) 6.24-6.58 (m, 3H) 3.70 (s, 3H) 2.83 (d, 3H); MS m/z (M+H) 274; (M−H) 272.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted five
  4. dry with materialorganics were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-6d1b3227884b4872a703b98f188b6dcd
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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