Formamide → 3-Methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide

HRID 437078Notes

Reaction equation

HRID 437078 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12]([O:14]C)=O)[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.C([NH2:18])=O.C[O-].[Na+].CCCCCC>Cl>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]([C:12]([NH2:18])=[O:14])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 713FormamideHCID 8058HexaneHCID 10942334Sodium MethoxideHCID 122789608-Quinolinecarboxylic acid, 5,6,7,8-tetrahydro-3-methyl-, methyl ester

Product 1

HCID 122782273-Methyl-5,6,7,8-tetrahydroquinoline-8-carboxamide

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of methyl 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate (25 g., 0.13 m), formamide (11.6, 0.26 m) and sodium methoxide (from 2.99 g., 0.13 m sodium) was heated with stirring in an oil bath at 120° from 1 hour. The reaction mixture was further heated at 100° for 3 hours under reduced pressure (15 mm Hg). The cooled reaction mixture was diluted with 2N HCl to give an acidic solution which was extracted with ethyl acetate (2× 50 ml.) and the combined extracts discarded. The aqueous solution was adjusted to pH 9.0 with solid Na2CO3, saturated with NaCl and extracted with chloroform (3× 100 ml.). The combined extracts were dried and evaporated to give a pale yellow oil which solidified on trituration with n-hexane. Recrystallisation from ethyl acetate gave the title compound as colourless cubes (18.6 g., 88%) m.p. 110°. Found: C, 69.6; H, 7.4; N, 14.4%. C11H14N2O requires: C, 69.5; H, 7.4; N, 14.7%.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was further heated at 100° for 3 hours under reduced pressure (15 mm Hg)
  3. customThe cooled reaction mixture
  4. customto give an acidic solution which
  5. extractionwas extracted with ethyl acetate (2× 50 ml.)
  6. extractionextracted with chloroform (3× 100 ml.)
  7. customThe combined extracts were dried
  8. customevaporated
  9. customto give a pale yellow oil which
  10. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-b032623be1384795bef2fdc870126b7a
Source dataset
uspto-grants-1977_06
Patent number
US04029668

Reaction notes

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