Water → HCID 21248633, compound

HRID 1194631Notes

Reaction equation

HRID 1194631 reaction equation
O.[Cl:2][C:3]1[C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[CH:7][C:6]([C:19]23[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]2[C:23](=[O:29])[NH:22][C:20]3=[O:21])=[C:5]([F:30])[CH:4]=1.C(OCC)C>C(O)(=O)C.[Fe]>[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][C:8]2[C:3]([Cl:2])=[CH:4][C:5]([F:30])=[C:6]([C:19]34[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]3[C:23](=[O:29])[NH:22][C:20]4=[O:21])[CH:7]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 21248634HCID 21248634, compound

Product 1

HCID 21248633HCID 21248633, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 20 mL of water in 200 mL of glacial acetic acid was added 6.0 g (0.014 mole) of 1-[4-chloro-2-fluoro-5-(4-nitrophenoxy)phenyl]-3,4,5,6-tetrahydrophthalimide. This mixture was stirred at room temperature while 6.0 g (0.11 mole) of iron filings were slowly added. After complete addition the mixture was stirred at room temperature for one hour. Diethyl ether was added and the resultant mixture was filtered through a pad of celite. The filtrate was washed with 200 mL of water. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving a solid. This solid was purified by column chromatography on silica gel, eluting with methylene chloride, to yield 4.0 g of 1-[5-(4-aminophenoxy)-4-chloro-2-fluorophenyl]-3,4,5,6-tetrahydrophthalimide as a solid, m.p. 213°-215° C.

Workup

  1. additionwere slowly added
  2. additionAfter complete addition the mixture
  3. filtrationthe resultant mixture was filtered through a pad of celite
  4. washThe filtrate was washed with 200 mL of water
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customleaving a solid
  9. customThis solid was purified by column chromatography on silica gel
  10. washeluting with methylene chloride

Sources & evidence

ORD record
ord-316abf3b16d545b5b087c8dcf1fc0c90
Source dataset
uspto-grants-1989_03
Patent number
US04816065

Reaction notes

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