Ethylamine → HCID 20063305, compound

HRID 1084409Notes

Reaction equation

HRID 1084409 reaction equation
[CH2:1](N)C.Cl[C:5]1[C:14]([C:15]([C:17](=[CH:23][N:24](C)[CH3:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])=[CH:13][C:12]2[C:7](=[C:8]([F:29])[C:9]([F:28])=[C:10]([F:27])[CH:11]=2)[N:6]=1>C(O)C>[CH2:21]([O:20][C:18]([C:17]1[C:15](=[O:16])[C:14]2[CH:13]=[C:12]3[CH:11]=[C:10]([F:27])[C:9]([F:28])=[C:8]([F:29])[C:7]3=[N:6][C:5]=2[N:24]([CH2:25][CH3:1])[CH:23]=1)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 53994177Ethyl 2-(2-chloro-6,7,8-trifluoro-3-quinolinecarbonyl)(dimethylamino)acrylate

Product 1

HCID 20063305HCID 20063305, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.5 g of ethylamine are added in the course of 10 minutes, at between 5° and 10° C., to a stirred suspension of 7.1 g of ethyl 2-(2-chloro-6,7,8-trifluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate in 100 cm3 of ethanol kept at a temperature close to 5° C., the mixture is stirred for 1 hour at between 5° and 10° C. and the temperature is allowed to rise to about 20° C. 4 g of 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU) are added to the solution obtained and the mixture is heated at a temperature close to 75° C. for 1 hour and a half. After cooling to a temperature close to 20° C., the product is drained and washed with twice 30 cm3 of ethanol and twice 50 cm3 of diisopropyl ether. 4 g of 3-ethoxycarbonyl-1-ethyl-7,8,9-trifluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine are obtained in the form of a cream solid melting at 284° C., which is used for the subsequent steps without further purification.

Workup

  1. customclose to 5° C.
  2. customto rise to about 20° C
  3. customobtained
  4. temperaturethe mixture is heated at a temperature
  5. customclose to 75° C. for 1 hour
  6. temperatureAfter cooling to a temperature
  7. customclose to 20° C.
  8. washwashed with twice 30 cm3 of ethanol and twice 50 cm3 of diisopropyl ether

Sources & evidence

ORD record
ord-3187d93f115e4127a8b1ec5ccc5c7b74
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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