Water → HCID 11611418, compound

HRID 902778Notes

Reaction equation

HRID 902778 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([O-:9])=[O:8])=[CH:5][CH:4]=1)=O.[NH2:12][C:13]1[CH:25]=[CH:24][C:16]2[O:17][C:18]([CH3:23])([CH3:22])[O:19][C:20](=[O:21])[C:15]=2[CH:14]=1.O>C1(C)C=CC=CC=1>[CH3:23][C:18]1([CH3:22])[O:17][C:16]2[CH:24]=[CH:25][C:13]([NH:12][CH2:1][C:3]3[CH:11]=[CH:10][C:6]([C:7]([O:9][CH2:1][C:3]4[CH:11]=[CH:10][CH:6]=[CH:5][CH:4]=4)=[O:8])=[CH:5][CH:4]=3)=[CH:14][C:15]=2[C:20](=[O:21])[O:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 4289537HCID 4289537, compoundHCID 116153306-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one

Product 1

HCID 11611418HCID 11611418, compoundYield 105.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-formylbenzoate (481 mg) and 6-amino-2,2-dimethyl-4H-1,3-benzodioxin-4-one (386 mg) in toluene (20 mL) was heated at reflux for 12 h with azeotropic removal of water. The toluene was evaporated off under reduce pressure, the residue was taken up in methanol (10 mL) and cooled to 0° C. NaBH4 (114 mg) was added portionwise and the reaction mixture was stirred at 0° C. for 1 h then at rt for 2 h. The reaction mixture was poured into water and resulting mixture extracted with Et2O. The combined organic layers were washed with brine, dried over MgSO4 and filtered. The solvent was removed under reduce pressure to give the crude product as an oil. The product was purified by flash chromatography (SiO2, EtOAc/c-Hex 20/80) to give the title compound as a colorless oil (713 mg, 85%). 1H NMR (CDCl3) δ 8.07 (d, J=8.1 Hz, 2H), 7.54-7.32 (m, 7H), 7.17 (d, J=2.6 Hz, 1H), 6.89-6.78 (m, 2H), 5.37 (s, 2H), 4.41 (s, 2H), 1.70 (s, 6H). M+(ESI): 418.3; M−(ESI): 416.1. HPLC, Rt: 4.6 min (purity: 95.8%).

Workup

  1. customThe toluene was evaporated off
  2. additionNaBH4 (114 mg) was added portionwise
  3. waitat rt for 2 h
  4. additionThe reaction mixture was poured into water
  5. customresulting mixture
  6. extractionextracted with Et2O
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe solvent was removed
  11. customto give the crude product as an oil
  12. customThe product was purified by flash chromatography (SiO2, EtOAc/c-Hex 20/80)

Sources & evidence

ORD record
ord-c64b4e056a6c47c9a5dc47981468a152
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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