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

HRID 442143Notes

Reaction equation

HRID 442143 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+]>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

5

Reactant 3

HCID 713FormamideHCID 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-carboxamideYield 90%

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 g., 0.26 m) and sodium methoxide (from 2.99 g., 0.13 m sodium) was heated on a steam bath for 1 hour while bubbling nitrogen through the mixture, to blow off the methyl formate produced in the reaction. The cooled reaction mixture was diluted with 2N HCl and worked up as described in Example 21 to give the title compound in 90% yield.

Workup

  1. temperaturewas heated on a steam bath for 1 hour
  2. customwhile bubbling nitrogen through the mixture
  3. customproduced in the reaction
  4. customThe cooled reaction mixture

Sources & evidence

ORD record
ord-e5f48d6a8ae440e794928fe6b85fa8a4
Source dataset
uspto-grants-1977_08
Patent number
US04044138

Reaction notes

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