Potassium Hydroxide → HCID 21945946, compound

HRID 1609898Notes

Reaction equation

HRID 1609898 reaction equation
C[O:2][C:3]([C:5]1[C:6]([CH3:24])=[C:7]2[N:12]([CH:13]=1)[N:11]=[CH:10][N:9]=[C:8]2[CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:23])=[O:4].[OH-].[K+]>CO>[O:23]=[C:15]1[CH:14]([C:8]2[C:7]3=[C:6]([CH3:24])[C:5]([C:3]([OH:4])=[O:2])=[CH:13][N:12]3[N:11]=[CH:10][N:9]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23589580HCID 23589580, compound

Product 1

HCID 21945946HCID 21945946, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Example 77 (3.3 g, 10.2 mmol) in methanol (600 mL) was added potassium hydroxide (1N aqueous solution, 200 mL) and the mixture was deoxygenated by purging with argon. The reaction mixture was heated to 60° C. for 20 hrs. The reaction mixture was cooled and concentrated to about 50 mL and the residue was acidified with concentrated HCl to pH 4. The yellow solid was collected, washed with water, and dried in vacuo to afford the title compound (2.9 g, 92%). MS: [M+H]+ =307.1; 1H NMR (CD3OD): δ 7.94 (s, 1H), 7.71 (s, 1H), 7.18-7.10 (m, 2H), 6.94-6.86 (m, 2H), 2.45 (s, 3H).

Workup

  1. customthe mixture was deoxygenated
  2. customby purging with argon
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated to about 50 mL
  5. customThe yellow solid was collected
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3d9fcf03f5bf42af87943013f61dd1b8
Source dataset
uspto-grants-2006_01
Patent number
US06982265B1

Reaction notes

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