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

HRID 596480Notes

Reaction equation

HRID 596480 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-f84e9dc5b07a4d198dd585908e39975f
Source dataset
uspto-grants-1977_03
Patent number
US04011225

Reaction notes

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