2,7,9-Trimethoxy-5,11-dioxa-benzo[b]fluoren-10-one → HCID 178515280, compound

HRID 411663Notes

Reaction equation

HRID 411663 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[O:8][C:9]4[CH:20]=[C:19]([O:21]C)[CH:18]=[C:17]([O:23]C)[C:10]=4[C:11](=[O:16])[C:12]=3[O:13][C:14]=2[CH:15]=1.N1C(=O)CC[C@H]1C(O)=O.Cl>O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[O:8][C:9]4[CH:20]=[C:19]([OH:21])[CH:18]=[C:17]([OH:23])[C:10]=4[C:11](=[O:16])[C:12]=3[O:13][C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 101498182,7,9-Trimethoxy-5,11-dioxa-benzo[b]fluoren-10-oneHCID 67725173Pyr-HCl

Product 1

HCID 178515280HCID 178515280, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Example 33 (0.90 g, 2.8 mmol) and Pyr-HCl (5 g) were heated together at 200° C. for 2 h. The reaction was cooled and diluted with water and the resultant solid filtered off. The solid thus obtained was triturated with MeOH, filtered, and triturated with EtOAc and then CH2Cl2. The resulting pink solid was dissolved in CH3OH/EtOAc (200 mL) and silica gel added. The solution was filtered and concentrated and the resulting solid triturated with CH3OH and then CH2Cl2. The product 36 was isolated as an off-white solid (0.35 g): Mp>300° C.; 1H NMR (DMSO-d6) δ 12.71 (s, 1H), 10.88 (s, 1H), 10.71 (s, 1H), 7.85 (d, 1H, J=8.7 Hz), 7.12 (d, 1H, J=1.8 Hz), 7.0 (dd, 1H, J=8.7 Hz, 1.9 Hz), 6.56 (d, 1H, J=2.1 Hz), 6.27 (d, 1H, J=2.0 Hz); MS 283 (M−H)−.

Workup

  1. customwere heated together at 200° C. for 2 h
  2. temperatureThe reaction was cooled
  3. filtrationthe resultant solid filtered off
  4. customThe solid thus obtained
  5. customwas triturated with MeOH
  6. filtrationfiltered
  7. customtriturated with EtOAc
  8. dissolutionThe resulting pink solid was dissolved in CH3OH/EtOAc (200 mL)
  9. additionsilica gel added
  10. filtrationThe solution was filtered
  11. concentrationconcentrated
  12. customthe resulting solid triturated with CH3OH

Sources & evidence

ORD record
ord-50623ae4a6a84aa4a6d860201bdccce1
Source dataset
uspto-grants-2003_05
Patent number
US06559177B2

Reaction notes

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