Dimethylformamide → HCID 22478976, compound

HRID 736483Notes

Reaction equation

HRID 736483 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[C:9]1[C:13]([C:14](C(N)C2C=CC(C(O)=O)=CC=2)=[O:15])=[C:12]([CH3:27])[O:11][N:10]=1.[OH-:28].[Na+].CN([CH:33]=[O:34])C>CO>[Cl:1][C:2]1[C:3]2[C:9]3[C:13](=[C:12]([CH3:27])[O:11][N:10]=3)[C:14](=[O:15])[N:10]([CH2:9][C:3]3[CH:4]=[CH:5][C:6]([C:33]([OH:34])=[O:28])=[CH:7][CH:2]=3)[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 22478814HCID 22478814, compound

Product 1

HCID 22478976HCID 22478976, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred suspension at room temperature of 245 (795 mg, 2.05 mmol) in anhydrous DMF (10 ml) was added a solution of NaOH (409 mg, 10.22 mmol) in anhydrous MeOH (5.1 ml). Then, the reaction mixture was warmed up to 40° C. After 3 days, the reaction mixture was concentrated, diluted with water and acidified with 1N HCl until pH 5 in order to get a pale pinky precipitate. After 30 min, the suspension was filtered off and the cake was abundantly washed with water, and dried to afford the title compound 246 (679 mg, 1.84 mmol, 90% yield) as a pale pinky solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm): AB system (δA=7.92, δB=7.40, J=8.4 Hz, 4H), 7.56 (t, J=8.1 Hz, 1H), 7.47 (d, J=7.5 Hz, 1H), 7.31 (d, J=8.3 Hz, 1H), 5.59 (bs, 2H), 2.95 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with water
  3. customto get a pale pinky precipitate
  4. waitAfter 30 min
  5. filtrationthe suspension was filtered off
  6. washthe cake was abundantly washed with water
  7. customdried

Sources & evidence

ORD record
ord-b7b34ede6fb44cb98a92cba5542f9939
Source dataset
uspto-grants-2009_09
Patent number
US07595343B2

Reaction notes

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