HCID 66980583, compound → HCID 11722481, compound

HRID 272666Notes

Reaction equation

HRID 272666 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:14]=1[C:15](OC)=[O:16]>Cl.CO>[Cl:23][C:21]1[CH:20]=[CH:19][C:14]2[C:15](=[O:16])[NH:1][C:2]3[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=3[NH:12][C:13]=2[CH:22]=1

Participants

4

Reactant 1

HCID 66980583HCID 66980583, compound

Product 1

HCID 11722481HCID 11722481, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of Example 1A (0.43 g, 1.28 mmol) in 37% HCl (20 mL) and methanol (50 mL) was heated to reflux for 20 hours, cooled to room temperature, and filtered. The filter cake was washed with 1:1H2O/methanol and dried in a vacuum oven at 65° C. to provide 0.34 g (87%) of the desired product. MS (DCI) m/e 303 (M+H)+, 320 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 10.04 (s, 1H), 8.50 (s, 1H), 7.72 (d, J=8.5 Hz, 1H), 7.55-7.60 (m, 2H), 7.08 (d, J=2 Hz, 1H), 7.03 (d, J=8.1 Hz, 1H), 6.96 (dd, J=8.5, 2 Hz, 1H), 3.80 (s, 3H).

Workup

  1. temperatureto reflux for 20 hours
  2. filtrationfiltered
  3. washThe filter cake was washed with 1:1H2O/methanol
  4. customdried in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-2f52b007a0c745b7a785f0cb47fd1f55
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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