Hydrochloric Acid → HCID 12378164, compound

HRID 1395276Notes

Reaction equation

HRID 1395276 reaction equation
[OH:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]([CH3:13])[CH2:7][CH2:8][N:9]2[CH3:12])=[CH:4][CH:3]=1.[F:14][C:15]([F:25])([F:24])[C:16](=O)[CH2:17][C:18](OCC)=[O:19].C(O)C.Cl>[Cl-].[Zn+2].[Cl-].O>[O:19]=[C:18]1[O:1][C:2]2=[N:11][C:10]3[N:9]([CH3:12])[CH2:8][CH2:7][CH:6]([CH3:13])[C:5]=3[CH:4]=[C:3]2[C:16]([C:15]([F:25])([F:24])[F:14])=[CH:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 178428482HCID 178428482, compound

Product 1

HCID 12378164HCID 12378164, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

The following procedure is typical of that used to prepare the various azacoumarins. 7-Hydroxy-1,4-dimethyl-1,2,3,4-tetrahydro-1,8-naphthyridine (0.19 g.), 1.2 ml. of ethyl trifluoroacetoacetate, 50 mg. of anhydrous zinc chloride, and 10 ml. of absolute ethanol were refluxed for 40 hours. The cooled solution was poured with stirring into 50 ml. of water plus 3 ml. of hydrochloric acid; the yellow precipitate was filtered, washed with water, and dried (0.31 g., 95%). Solvent used for recrystallization, melting point, fluorescence data and analytical data are summarized in the table below. The 1H nmr spectral data (deuteriochloroform, 100 MHz) on the analogous 6,8,9-trimethyl derivative are: δ1.37 (d, 6H, CH3CH), 1.47 (m,1H, H7b), 2.10 (dt, 1H, H7a,J=13 Hz, J=4 Hz), 2.80 (m, 1H, H6), 3.20 (s, 3H, NCH3), 3.70 (m, 1H, H8), 6.38 (s, 1H, H3), 7.41 (q, 1H, H5, JH5 --CF3 =~1.5 Hz).

Workup

  1. additionThe cooled solution was poured
  2. filtrationthe yellow precipitate was filtered
  3. washwashed with water
  4. customdried (0.31 g., 95%)
  5. customSolvent used for recrystallization

Sources & evidence

ORD record
ord-4de67e7a9eab4f1689bc22062722248e
Source dataset
uspto-grants-1980_05
Patent number
US04202981

Reaction notes

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