HCID 66675207, compound → HCID 66673945, compound

HRID 423184Notes

Reaction equation

HRID 423184 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=3)[CH2:13][CH3:14])[C:10]3[CH:24]=[CH:25][CH:26]=[N:27][C:9]=3[CH2:8][O:7][C:6]=2[CH:28]=1>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[C:12]([C:15]3[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=3)[CH2:13][CH3:14])[C:10]3=[CH:24][CH:25]=[CH:26][NH:27][C:9]3=[CH:8][O:7][C:6]=2[CH:28]=1

Participants

3

Reactant 1

HCID 66675207HCID 66675207, compound

Product 1

HCID 66673945HCID 66673945, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-Fluoro-5-[1-(3-nitro-phenyl)-propylidene]-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cycloheptene (1.49 g, 3.96 mmol) is dissolved in ethanol (20 mL) and purged with nitrogen. Pd/C (0.15 g, 10%) is added and the mixture hydrogenated under 1 atm of hydrogen for 2 h. The mixture is purged with nitrogen, filtered though Celite®, and the solids are washed with ethanol. The filtrate is concentrated under reduced pressure to obtain 1.37 g (99%) of the title compound. LCMS m/e 347 [M+H]+.

Workup

  1. custompurged with nitrogen
  2. additionPd/C (0.15 g, 10%) is added
  3. customThe mixture is purged with nitrogen
  4. filtrationfiltered though Celite®
  5. washthe solids are washed with ethanol
  6. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d800f7f7ad5e4947b1e8202f4e5097ac
Source dataset
uspto-grants-2012_01
Patent number
US08101761B2

Reaction notes

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