Hydrochloric Acid → HCID 9885674, compound

HRID 634637Notes

Reaction equation

HRID 634637 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:24][C:23](=[O:25])[C:9]3[C:10](=[O:22])[NH:11][C:12]4[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][C:17]=4[C:8]=3[C:6]=2[CH:7]=1.CC(C[Al]CC(C)C)C.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:24])=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=3)[NH:11][C:10](=[O:22])[C:9]=2[CH2:23][OH:25])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10959481HCID 10959481, compoundHCID 16682954Dibah

Product 1

HCID 9885674HCID 9885674, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cold suspension (−78° C.) of 2-chloro-6,8-dihydro-11-(trifluoromethyl)-7H-[1]benzopyrano[3,4-c]quinolin-6,7-dione prepared in Step C (1.0 g, 2.73 mmol) in methylene chloride (20 mL), a solution of Dibal-H (1M in methylene chloride, 13.7 mL, 13.7 mmol) was added dropwise. The reaction mixture was warmed to 0° C. and maintained for 3 hours. The reaction mixture was acidified with 1N HCl and extracted with ethyl acetate twice. The organic layer was separated and washed with water, brine and then dried (MgSO4). Evaporation of the solvent followed by recrystallization of the crude product from ethyl acetate/hexanes afforded the title compound as a white solid (0.7 g, 69%): mp>250° C.; MS m/e 368 (M−H)−.

Workup

  1. temperaturemaintained for 3 hours
  2. extractionextracted with ethyl acetate twice
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent
  7. customfollowed by recrystallization of the crude product from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-51716e1802a440579c4a0f5f732541ce
Source dataset
uspto-grants-2001_02
Patent number
US06184231B2

Reaction notes

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