Hydrochloric Acid → HCID 12017669, compound

HRID 1006532Notes

Reaction equation

HRID 1006532 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)([O-])=O.C1COCC1.Cl>[Fe].O>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 12017668HCID 12017668, compound

Product 1

HCID 12017669HCID 12017669, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of methyl 4-(2-nitro-5-chlorophenylmethoxy)benzoate (460 mg; prepared in Reference Example 9.), THF (10 ml), water (3 ml), 1N HCl (0.4 ml) and iron powder (500 mg) was stirred for 13 hours. The reaction mixture was filtered. The filtrate was washed, dried over and concentrated under the reduced pressure. The residue was purified on silica gel column chromatography (hexane-AcOEt) to give the title compound (419 mg) having the following physical data.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washThe filtrate was washed
  3. customdried over and
  4. concentrationconcentrated under the reduced pressure
  5. customThe residue was purified on silica gel column chromatography (hexane-AcOEt)

Sources & evidence

ORD record
ord-89796d1148e24dc1abec41396a75d7c3
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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