Potassium Carbonate → HCID 13389002, compound

HRID 255497Notes

Reaction equation

HRID 255497 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:14]2[C:13](=[O:25])[NH:12][CH:11]=[CH:10][C:9]=2[NH:8][C:7]=1[CH3:26])=[O:5])[CH3:2].[CH3:27][N:28]([CH2:30][CH2:31][CH2:32]Cl)[CH3:29].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[CH2:1]([O:3][C:4]([C:6]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:14]2[C:13](=[O:25])[N:12]([CH2:32][CH2:31][CH2:30][N:28]([CH3:29])[CH3:27])[CH:11]=[CH:10][C:9]=2[NH:8][C:7]=1[CH3:26])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 13389001HCID 13389001, compound

Product 1

HCID 13389002HCID 13389002, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

6.9 g (19.4 mmol) of 1,4,5,6-tetrahydro-2-methyl-4-(3-nitrophenyl)-5-oxo-1,6-naphthyridine-3-carboxylic acid ethyl ester prepared according to Example 1, and 2.4 g (19.4 mmol) of N,N-dimethylaminopropylchloride are kept at boiling temperature for 48 hours with 10.7 g (77.6 mmol) potassium carbonate in 500 ml acetone. The product is reduced in volume to dryness under vacuum, the residue is taken up in 500 ml water and 500 ml methylene chloride and the organic phase washed with 500 ml water and dried over sodium sulfate. The brown crude product obtained after removing the solvent in vacuo is recrystallized twice from acetonitrile/ethanol. There is obtained 1,4,5,6-tetrahydro-6-(3-dimethylaminopropyl)-2-methyl-4-(3-nitrophenyl)-5-oxo-1,6-naphthyridine-3-carboxylic acid ethyl ester in the form of yellow needles with a melting point of 212°-213° C.

Workup

  1. customfor 48 hours
  2. wash500 ml methylene chloride and the organic phase washed with 500 ml water
  3. dry with materialdried over sodium sulfate
  4. customThe brown crude product obtained
  5. customafter removing the solvent in vacuo
  6. customis recrystallized twice from acetonitrile/ethanol

Sources & evidence

ORD record
ord-004e6ec23b1b497eac1d1de7a66663b2
Source dataset
uspto-grants-1987_10
Patent number
US04698341

Reaction notes

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