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

HRID 344863Notes

Reaction equation

HRID 344863 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].C(N(CC)CC)C.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:4]([O:2][CH3:3])[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

A suspension of methoxylamine hydrochloride (1.7 g) in trichloromethane (40 cc) is treated with triethylamine (2.13 g). After 15 minutes' stirring at a temperature in the region of 20° C., the solution obtained is treated with ethyl 2-(2-chloro-6,7-difluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (3.69 g) and stirred for 4 hours and a half at approximately 20° C. The reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at a temperature in the region of 50° C. The residue is taken up with ethanol (70 cc) and triethylamine (3.6 g) and heated for 30 minutes to a temperature in the region of 75° C. After cooling to approximately 20° C., the precipitate obtained is drained and washed with ethanol (3×30 cc). 3-Ethoxycarbonyl-7,8-difluoro-1-methoxy-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (2.67 g) is obtained in the form of a pale yellow solid, m.p. 266°-268° C.).

Workup

  1. customthe solution obtained
  2. stirringstirred for 4 hours
  3. customat approximately 20° C
  4. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (20 kPa) at a temperature in the region of 50° C
  5. temperatureheated for 30 minutes to a temperature in the region of 75° C
  6. temperatureAfter cooling to approximately 20° C.
  7. customthe precipitate obtained
  8. washwashed with ethanol (3×30 cc)

Sources & evidence

ORD record
ord-d6d129f3ce1f47e2a3c57ff4ad8ecbb9
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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