HCID 18421435, compound → HCID 18421395, compound

HRID 368793Notes

Reaction equation

HRID 368793 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): δ 7.73-7.97 (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-c700eb1b3d1e44f18b7b3cb5a1bd048c
Source dataset
uspto-grants-2000_10
Patent number
US06133460

Reaction notes

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