Hydrochloric Acid → HCID 20531187, compound

HRID 1759558Notes

Reaction equation

HRID 1759558 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[F:20].[C:21]([CH2:24][NH:25][CH:26]1[CH2:30][CH2:29][NH:28][CH2:27]1)(=[O:23])[CH3:22].C(N(CC)CC)C.Cl>C(Cl)(Cl)Cl>[C:21]([CH2:24][NH:25][CH:26]1[CH2:30][CH2:29][N:28]([C:2]2[N:11]=[C:10]3[C:5]([C:6](=[O:19])[C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][N:9]3[CH2:12][CH3:13])=[CH:4][C:3]=2[F:20])[CH2:27]1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2781265HCID 2781265, compoundHCID 20531188HCID 20531188, compound

Product 1

HCID 20531187HCID 20531187, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture containing ethyl 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (2.99 g), 3-(N-acetylmethylamino)pyrrolidine (2.13 g), triethylamine (1.52 g), and chloroform (30 ml) was heated to reflux for 4 hours with stirring. After cooling the mixture, 5% hydrochloric acid (20 ml) was added with stirring. The chloroform layer was separated off and the solvent was evaporated. To the residue was added 20 ml of acetonitrile and the mixture was cooled. The resulting precipitate was collected and recrystallized from acetonitrile to give 3.51 g of ethyl 7-[3-(N-acetylmethylamino)-1-pyrrolidinyl]-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, m.p. 212°-213° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. additionwas added
  4. stirringwith stirring
  5. customThe chloroform layer was separated off
  6. customthe solvent was evaporated
  7. additionTo the residue was added 20 ml of acetonitrile
  8. temperaturethe mixture was cooled
  9. customThe resulting precipitate was collected
  10. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-130c7483f7234a46841a59ae1a09e3af
Source dataset
uspto-grants-1982_07
Patent number
US04341784

Reaction notes

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