HCID 22605917, compound → HCID 22605915, compound

HRID 2307272Notes

Reaction equation

HRID 2307272 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N+:3]=1[O-]>[Fe].C(O)(=O)C>[Br:1][C:2]1[CH:11]=[C:10]([NH2:12])[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

4

Reactant 1

HCID 22605917HCID 22605917, compound

Product 1

HCID 22605915HCID 22605915, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromo-4-nitro-5,6,7,8-tetrahydro-quinoline 1-oxide (example 7a) (7.9 g, 28.9 mmol), powdered iron (13.3 g, 238 mmol) and acetic acid (160 ml) was heated to 100° C. for 1 hr. After cooling the mixture was filtered and evaporated and the residue was partitioned (AcOEt/NaHCO3-solution). The organic phase was dried (Na2SO4), concentrated and chromatographed (SiO2 with CH2Cl2/MeOH=98/2) to provide 2.4 g (37%) of the title compound as a brown solid material. MS: m/e=226 (M+).

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationwas filtered
  3. customevaporated
  4. customthe residue was partitioned (AcOEt/NaHCO3-solution)
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated
  7. customchromatographed (SiO2 with CH2Cl2/MeOH=98/2)

Sources & evidence

ORD record
ord-f68aadcfa0ec4439adf388c0b3011dc4
Source dataset
uspto-grants-2004_12
Patent number
US06831087B2

Reaction notes

Loading…