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methyl 2-fluoro-4-{[(6-nitro-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate → methyl 4-{[(6-amino-2,3-dihydro-1H-inden-5-yl)oxy]methyl}-2-fluorobenzoate

HRID 1879402
Notes
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Reaction equation

HRID 1879402 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][C:22]=2[N+:23]([O-])=O)[CH2:19][CH2:18][CH2:17]3)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>C(O)(=O)C.O>[NH2:23][C:22]1[CH:21]=[C:20]2[C:16]([CH2:17][CH2:18][CH2:19]2)=[CH:15][C:14]=1[O:13][CH2:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 58398391methyl 2-fluoro-4-{[(6-nitro-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate

Product 1

HCID 58398429methyl 4-{[(6-amino-2,3-dihydro-1H-inden-5-yl)oxy]methyl}-2-fluorobenzoateYield 60.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

11.0 g of methyl 2-fluoro-4-{[(6-nitro-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate was dissolved in 120 mL of acetic acid and 12.0 mL of water, and 8.89 g of reduced iron was added thereto at 60° C., followed by stirring at 60° C. for 4.5 hours. The reaction liquid was cooled to room temperature, and then filtered through Celite, and the filtrate was concentrated under reduced pressure. The obtained residue was suspended in water and ethyl acetate, neutralized by the addition of sodium hydrogen carbonate, and then filtered through Celite. After the filtrate was extracted with ethyl acetate, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=95:5 to 90:10) to obtain 6.06 g of methyl 4-{[(6-amino-2,3-dihydro-1H-inden-5-yl)oxy]methyl}-2-fluorobenzoate.

Workup

  1. customat 60° C.
  2. customThe reaction liquid
  3. temperaturewas cooled to room temperature
  4. filtrationfiltered through Celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionethyl acetate, neutralized by the addition of sodium hydrogen carbonate
  7. filtrationfiltered through Celite
  8. extractionAfter the filtrate was extracted with ethyl acetate
  9. washthe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated
  12. customthe obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=95:5 to 90:10)

Sources & evidence

ORD record
ord-7a475fda60b4429b95d1c36da2fc7155
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08314240B2

Reaction notes

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