HCID 18421435, compound → HCID 18421395, compound

HRID 1281649Notes

Reaction equation

HRID 1281649 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH2:16]Br)[C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K]>CN(C=O)C>[C:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[C:10]([CH2:16][N:22]3[C:21](=[O:23])[C:20]4=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]4[C:18]3=[O:28])[C:11](=[O:15])[O:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 18421435HCID 18421435, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 18421395HCID 18421395, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-acetoxy-3-bromomethylcoumarin (630 mg) was stirred overnight with potassium phthalimide (432 mg, 2.33 mmol) in DMF (100 mL). The reaction solvent was evaporated and the reaction partitioned between CH2Cl2 and water, then washed several times with water, then with aqueous NaHCO3. The organic layer was dried with brine, then with anhydrous sodium sulfate and evaporated. The crude product was recrystallized in acetic acid to give 7-acetoxy-3-phthalimidomethylcoumarin (375 mg, >95% purity), an off-white solid. 1H NMR (CDCl3): δ7.73-7.97 (m, 4H), 7.53 (s, 1H), 7.43 (d, J=8.4 Hz, 1H), 7.13 (s, 1H), 7.03 (dd, J=7.5, 2.1, 1H), 4.82 (s, 2H), 2.33 (s, 3H).

Workup

  1. customThe reaction solvent was evaporated
  2. customthe reaction partitioned between CH2Cl2 and water
  3. washwashed several times with water
  4. dry with materialThe organic layer was dried with brine
  5. customwith anhydrous sodium sulfate and evaporated
  6. customThe crude product was recrystallized in acetic acid

Sources & evidence

ORD record
ord-ba94d780071340978890f758a118c2db
Source dataset
uspto-grants-2002_09
Patent number
US06455286B1

Reaction notes

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