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

HRID 2083417Notes

Reaction equation

HRID 2083417 reaction equation
C[O:2][C:3]([CH:5]1[C:14]2[N:13]=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[CH2:8][CH2:7][CH2:6]1)=O.C([NH2:18])=O.C[O-].[Na+].CCCCCC>Cl>[CH3:15][C:11]1[CH:12]=[N:13][C:14]2[CH:5]([C:3]([NH2:18])=[O:2])[CH2:6][CH2:7][CH2:8][C:9]=2[CH:10]=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., 0.13m sodium) was heated with stirring in an oil bath at 120° for 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 ethylacetate (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 ethylacetate gave the title compound as colourless cubes (18.6 g., 88%) m.p. 110°. Found: C, 69.6; H, 7.4; N, 14.4%. C11H 14 N2O 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 ethylacetate (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 ethylacetate

Sources & evidence

ORD record
ord-76889c28f9954040a16dc649f97c7829
Source dataset
uspto-grants-1978_04
Patent number
US04085215

Reaction notes

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