Triethylamine → 3-Ethoxycarbonyl-7,8-difluoro-1-methoxy-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 1084384Notes

Reaction equation

HRID 1084384 reaction equation
C(N(CC)CC)C.Cl.[O:9]([NH2:11])[CH3:10].Cl[C:13]1[C:22]([C:23]([C:25](=[CH:31]N(C)C)[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:24])=[CH:21][C:20]2[C:15](=[CH:16][C:17]([F:36])=[C:18]([F:35])[CH:19]=2)[N:14]=1>ClC(Cl)Cl>[CH2:29]([O:28][C:26]([C:25]1[C:23](=[O:24])[C:22]2[CH:21]=[C:20]3[CH:19]=[C:18]([F:35])[C:17]([F:36])=[CH:16][C:15]3=[N:14][C:13]=2[N:11]([O:9][CH3:10])[CH:31]=1)=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 53731972Ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3-dimethylaminoacrylate

Product 1

HCID 148533423-Ethoxycarbonyl-7,8-difluoro-1-methoxy-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 79.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

2.13 g of triethylamine are added to a suspension of 1.7 g of methoxylamine hydrochloride in 40 cm3 of trichloromethane. After stirring for 15 minutes at a temperature close to 20° C., 3.69 g of ethyl 2-(2-chloro-6,7-difluoroquinoline-3-carbonyl)-3dimethylaminoacrylate are added to the solution obtained and the mixture is stirred for 4 hours and a half at about 20° C. The reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at a temperature close to 50° C. The residue is taken up in 70 cm3 of ethanol and 3.6 g of triethylamine and the mixture is heated for 30 minutes at a temperature close to 75° C. After cooling to about 20° C., the precipitate obtained is drained and washed with 3 times 30 cm3 of ethanol. 2.67 g of 3-ethoxycarbonyl-7,8-difluoro-1-methoxy-4-oxo-1,4-dihydro-benzo[b] [1,8]naphthyridine are obtained in the form of a pale yellow solid melting at 266°-268° C.

Workup

  1. customclose to 20° C.
  2. customobtained
  3. stirringthe mixture is stirred for 4 hours
  4. customat about 20° C
  5. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at a temperature
  6. customclose to 50° C
  7. temperature3.6 g of triethylamine and the mixture is heated for 30 minutes at a temperature
  8. customclose to 75° C
  9. customthe precipitate obtained
  10. washwashed with 3 times 30 cm3 of ethanol

Sources & evidence

ORD record
ord-9c80f05c8a4043bfabc008abff440a4e
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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