Water → HCID 24780523, compound

HRID 2241803Notes

Reaction equation

HRID 2241803 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)=[CH:4][N:3]=1.O.[CH3:21][N:22](C=O)[CH3:23]>S(=O)(=O)(O)O>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]2[N:8]=[C:6]([C:5]3[CH:18]=[CH:19][C:2]([N:22]([CH3:23])[CH3:21])=[N:3][CH:4]=3)[O:17][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 59203847HCID 59203847, compound

Product 1

HCID 24780523HCID 24780523, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

6-Chloro-N-(2-hydroxy-4-methoxyphenyl)nicotinamide (40 mg, 0.14 mmol) was dissolved in DMF (1.5 mL) and one drop of sulfuric acid was added. The reaction was run at 230° C. for 20 minutes in a microwave reactor. The mixture was added to water, the solid was collected, rinsed with water and dried. The crude product was purified by flash column chromatography using 40% ethyl acetate in hexane, giving the title compound (14 mg) as an orange solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.96 (d, 1H) 8.19 (dd, 1 H) 7.57 (d, 1H) 7.10 (d, 1H) 6.92 (dd, 1H) 6.60 (d, 1H) 3.88 (s, 3H) 3.20 (s, 6H); MS m/z (M+H) 270.

Workup

  1. customthe solid was collected
  2. washrinsed with water
  3. customdried
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-98a6bc0f06ab4ea683206b64f38480ad
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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