HCID 69271080, compound → HCID 68509445, compound

HRID 2221116Notes

Reaction equation

HRID 2221116 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[C:18]3[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=3[O:16][CH:15]=2)=[CH:8][C:7]=1[N+:24]([O-])=O)[CH3:2]>C(O)C.Cl.[Fe]>[CH2:1]([O:3][C:4](=[O:27])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][C:14]2[C:18]3[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=3[O:16][CH:15]=2)=[CH:8][C:7]=1[NH2:24])[CH3:2]

Participants

5

Reactant 1

HCID 69271080HCID 69271080, compound

Product 1

HCID 68509445HCID 68509445, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

{4-[(5-Fluoro-benzofuran-3-ylmethyl)-amino]-2-nitro-phenyl}-carbamic acid ethyl ester (4.50 g, 12.1 mmol) was dissolved in absolute ethanol (140 mL) whereto 6N aqueous HCl (38 mL) and iron powder (5.70 g, 0.10 mol) was added. The red mixture was heated at 60° C. until the intense colour disappeared (20 minutes). The solids were filtered off and the ethanol was removed from the filtrate by evaporation in vacuo. Aqueous ammonia (saturated) was added to the remanence, which was then extracted with ethyl acetate (3×100 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography on silica gel (eluent:ethyl acetate:heptane 1:1) to furnish 2.70 g (66%) of the title compound as a solid. M.p. 150-151° C. Calculated for C18H18FN3O3: C, 62.96; H, 5.28; N, 12.24. Found: C, 63.00; H, 5.38; N, 12.13. LC/MS (m/z) 344 (MH+); tR=2.00 min. 1H NMR (DMSO-d6): 1.19 (t, 3H); 4.03 (q, 2H); 4.26 (d, 2H); 4.55 (s, 2H, NH2); 5.79 (t, 1H); 5.91 (dd, 1H); 6.02 (d, 1H, NH); 6.72 (d, 1H); 7.13 (dt, 1H); 7.56 (m, 2H); 7.95 (s, 1H); 8.16 (b, 1H, NH).

Workup

  1. additionwas added
  2. custom(20 minutes)
  3. filtrationThe solids were filtered off
  4. customthe ethanol was removed from the filtrate by evaporation in vacuo
  5. additionAqueous ammonia (saturated) was added to the remanence, which
  6. extractionwas then extracted with ethyl acetate (3×100 mL)
  7. washThe combined organic fractions were washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by chromatography on silica gel (eluent:ethyl acetate:heptane 1:1)

Sources & evidence

ORD record
ord-e335eadcb70e4cd2839e1f6dc89f5e60
Source dataset
uspto-grants-2008_05
Patent number
US07368472B2

Reaction notes

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