alpha-Cyano-beta-(2-Nitro-5-Fluorophenyl)Acrylamide → 6-Fluoro-2-Aminoquinoline-3-Carboxamide

HRID 1112243Notes

Reaction equation

HRID 1112243 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[N+:15]([O-])=O)[C:4]([NH2:6])=[O:5])#[N:2]>C(O)(=O)C.[Fe]>[F:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][CH:11]=1)[N:15]=[C:1]([NH2:2])[C:3]([C:4]([NH2:6])=[O:5])=[CH:7]2

Participants

4

Reactant 1

HCID 53864188alpha-Cyano-beta-(2-Nitro-5-Fluorophenyl)Acrylamide

Product 1

HCID 227528386-Fluoro-2-Aminoquinoline-3-Carboxamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 176Acetic AcidSolvent

Procedure

Iron powder (8.52 g., 0.152 mole) is gradually added over a 40-minute period to a slurry of α-cyano-β-(2-nitro-5-fluorophenyl)acrylamide (7.97 g., 0.034 mole) in acetic acid (100 ml.) at 85° C. When addition of the iron powder is complete, the mixture is heated to 95°-100° C. for 1.5 hours and then filtered hot through diatomaceous earth. The filtrate is cooled in an ice bath and then filtered to give a tan crystalline solid. The solid is partitioned between ethyl acetate and water, the organic phase separated, dried over anhydrous sodium sulfate and concentrated to yield 6.34 g. (90%) of the title amide as yellow crystals. M.P. 232°-236° C.

Workup

  1. temperaturethe mixture is heated to 95°-100° C. for 1.5 hours
  2. filtrationfiltered hot through diatomaceous earth
  3. temperatureThe filtrate is cooled in an ice bath
  4. filtrationfiltered
  5. customto give a tan crystalline solid
  6. customThe solid is partitioned between ethyl acetate and water
  7. customthe organic phase separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customto yield 6.34 g

Sources & evidence

ORD record
ord-2a16d4f120d446dcb8f9b6fc95cafb3f
Source dataset
uspto-grants-1978_10
Patent number
US04120962

Reaction notes

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