HCID 18476046, compound → HCID 18476013, compound

HRID 2187616Notes

Reaction equation

HRID 2187616 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O>C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([C:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

3

Reactant 1

HCID 18476046HCID 18476046, compound

Product 1

HCID 18476013HCID 18476013, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-nitro-6-(4-fluorobenzyl)benzoate (10 g, 36.9 mmol) in ethyl acetate (740 ml) was treated with stannous chloride dihydrate (41.6 g, 184.5 mmol). The mixture was refluxed for 17 hours, evaporated to 300 ml and aqueous ammonia (S.G. 0.88) added to pH 10. The resulting suspension filtered, washed with ethyl acetate and evaporated to give a yellow oil which was purified by flash chromatography (ethyl acetate/ iso-hexane: 1/1) to give methyl 3-amino-6-(4-fluorobenzyl)benzoate (7.54 g; 85%)

Workup

  1. temperatureThe mixture was refluxed for 17 hours
  2. customevaporated to 300 ml and aqueous ammonia (S.G. 0.88)
  3. additionadded to pH 10
  4. filtrationThe resulting suspension filtered
  5. washwashed with ethyl acetate
  6. customevaporated
  7. customto give a yellow oil which
  8. customwas purified by flash chromatography (ethyl acetate/ iso-hexane: 1/1)

Sources & evidence

ORD record
ord-6045e9f5293d4ac98d8dc71386e3aaeb
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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