HCID 86584083, compound → HCID 21956379, compound

HRID 989392Notes

Reaction equation

HRID 989392 reaction equation
[C:1](/[C:3](=[CH:8]\[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH2:18][CH2:19][Cl:20])=[CH:11][C:10]=1[N+:21]([O-])=O)/[C:4]([O:6][CH3:7])=[O:5])#[N:2]>C(O)(=O)C.[Fe]>[NH2:2][C:1]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][C:9]2[C:10](=[CH:11][C:12]([O:17][CH2:18][CH2:19][Cl:20])=[C:13]([O:15][CH3:16])[CH:14]=2)[N:21]=1

Participants

4

Reactant 1

HCID 86584083HCID 86584083, compound

Product 1

HCID 21956379HCID 21956379, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To methyl (2E)-2-cyano-3-[4-(2-chloroethoxy)-5-methoxy-2-nitrophenyl]-2-propenoate (19.3 g, 56.6 mmol) in 250 mL of acetic acid is added portionwise 12.0 g (215.0 mmol) of iron. The mixture is heated at reflux for 20 minutes, cooled slightly and filtered washing with ethyl acetate. The filtrate is concentrated in vacuo and water is added to the residue. The resulting yellow solid is collected by filtration washing with water to provide 14.6 g of methyl 2-amino-7-[2-chloroethoxy]-6-methoxy-3-quinolinecarboxylate. An analytical sample is obtained by stirring a portion of the product with a mixture of methanol and aqueous ammonium hydroxide. The undissolved solids are removed by filtration. Upon standing solids appeared in the filtrate and are collected to provide methyl 2-amino-7-[2-chloroethoxy]-6-methoxy-3-quinolinecarboxylate as light yellow crystals, mp 145-157° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 20 minutes
  3. temperaturecooled slightly
  4. filtrationfiltered
  5. washwashing with ethyl acetate
  6. concentrationThe filtrate is concentrated in vacuo and water
  7. additionis added to the residue
  8. filtrationThe resulting yellow solid is collected by filtration
  9. washwashing with water

Sources & evidence

ORD record
ord-7b692ed9ec0c44d0bdbec772f8b9fe3b
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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