Hydrochloric Acid → HCID 58307563, compound

HRID 1516454Notes

Reaction equation

HRID 1516454 reaction equation
[F:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-])=O)[CH:3]=1.Cl>C(O)C.[Fe]>[F:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([NH2:11])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58307564HCID 58307564, compound

Product 1

HCID 58307563HCID 58307563, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Compound 7 (1.4 g, 7.64 mmol) was suspended in ethanol (51 mL). Iron (2.57 g, 45.85 mmol) and conc. HCl (4 mL) was added at 0° C. The resulting suspension was stirred overnight at room temperature. The reaction was quenched by addition of NaHCO3. The crude was extracted with ethyl acetate. It was purified by column chromatography, eluted at 25% ethyl acetate/hexane, to yield the desired compound 8 (1.09 g, yield 93.1%).

Workup

  1. customThe reaction was quenched by addition of NaHCO3
  2. extractionThe crude was extracted with ethyl acetate
  3. customIt was purified by column chromatography
  4. washeluted at 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d3dd3e8c606242f180f61be3f7acbbbc
Source dataset
uspto-grants-2012_07
Patent number
US08227501B2

Reaction notes

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