Dimethylamine → 4-Dimethylamino-6-aminoquinaldine

HRID 479327Notes

Reaction equation

HRID 479327 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH3:15])[CH:9]=[C:8]2OC)(=O)C.[CH3:18][NH:19][CH3:20]>C(O)(=O)C>[CH3:18][N:19]([CH3:20])[C:8]1[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([NH2:4])[CH:6]=2)[N:11]=[C:10]([CH3:15])[CH:9]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 4785621N-(4-methoxy-2-methylquinolin-6-yl)acetamide

Product 1

HCID 179088824-Dimethylamino-6-aminoquinaldineYield 77%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The procedure is carried out as in Step A of Example 6, but starting with 57.4 g (0.25 mol) of 6-acetamido-4-methoxyquinaldine, prepared according to J. Amer. Chem. Soc., 1948, 70, 4065, and 100 cm3 of a 40% aqueous dimethylamine solution in 250 cm3 of acetic acid heated at 100° C. for 2 hours in a 1-dm3 autoclave. 38.71 g (77%) of 4-dimethylamino-6-aminoquinaldine are then obtained, after acid-base purification, on carrying out the procedure as in Step A of Example 6.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-c6dc368dd88d4c91af2008662cdb29af
Source dataset
uspto-grants-2003_11
Patent number
US06645964B1

Reaction notes

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