2-Cyano-3-[5-(methylsulfanyl)-2-nitrophenyl]prop-2-enamide → 6-Methylthio-2-Aminoquinoline-3-Carboxamide

HRID 1283171Notes

Reaction equation

HRID 1283171 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[C:12]([S:14][CH3:15])[CH:11]=[CH:10][C:9]=1[N+:16]([O-])=O)[C:4]([NH2:6])=[O:5])#[N:2]>C(O)(=O)C.CN(C)C=O.[Fe]>[CH3:15][S:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][CH:11]=1)[N:16]=[C:1]([NH2:2])[C:3]([C:4]([NH2:6])=[O:5])=[CH:7]2

Participants

4

Reactant 1

HCID 539198542-Cyano-3-[5-(methylsulfanyl)-2-nitrophenyl]prop-2-enamide

Product 1

HCID 227528206-Methylthio-2-Aminoquinoline-3-Carboxamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 21926011acetic acid N,N-dimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of α-cyano-β-(2-nitro-5-methylthiophenyl)acrylamide (8.4 g., 0.032 mole) in acetic acid - N,N-dimethylformamide (110 ml. of 1:1) is heated in a 75°C. bath. Iron powder (2.0 g.) is added and the mixture stirred until the internal temperature rose to 95°C. Additional iron powder (6.16 g. total iron added=0.146 mole) is added in small portions over a fifteen-minute period. The reaction mixture is stirred for one hour following completion of addition and then filtered hot. The iron residue is washed with hot acetic acid and the combined filtrate and wash solution poured into IN hydrochloric acid (200 ml.) The hydrochloride salt which separates is filtered off and dissolved in hot dilute sodium hydroxide. The yellow solid which separates on cooling is filtered off, washed with isopropyl alcohol and air-dried. Yield = 3.26 g. (44%), M.P. 229°-242°C.

Workup

  1. customrose to 95°C
  2. stirringThe reaction mixture is stirred for one hour
  3. additioncompletion of addition
  4. filtrationfiltered hot
  5. washThe iron residue is washed with hot acetic acid
  6. washthe combined filtrate and wash solution
  7. additionpoured into IN hydrochloric acid (200 ml.) The hydrochloride salt which
  8. filtrationseparates is filtered off
  9. dissolutiondissolved in hot dilute sodium hydroxide
  10. temperatureon cooling
  11. filtrationis filtered off
  12. washwashed with isopropyl alcohol
  13. customair-dried

Sources & evidence

ORD record
ord-3e226cef41a24430981d6fcc0efbee32
Source dataset
uspto-grants-1976_08
Patent number
US03974161

Reaction notes

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