Ethyl 4,4,4-trifluoroacetoacetate → HCID 12378169, compound

HRID 1395277Notes

Reaction equation

HRID 1395277 reaction equation
[NH2:1][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]>>[O:19]=[C:18]1[NH: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

3

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 12378162HCID 12378162, compound

Product 1

HCID 12378169HCID 12378169, compound

Procedure

This is a representative procedure for making azaquinolones. 7-Amino-1,4-dimethyl-1,2,3,4-tetrahydro-1,8-naphthyridine (0.9 g.) and 1.0 g. of ethyl trifluoroacetoacetate were heated at 145°-165° for 18 hours. The cooled, semisolid mass was slurried with 5 ml. of ether, filtered and washed with more ether, 1.3 g., m.p. 225°-230°, wet 200°. Other data are found in the table. 1H nmr (deuteriochloroform, 100 MHz): δ1.30 (d,3H, CH3CH, J=7 Hz), 1.74 (m, 1H, H7a or H7b), 1.89 (m, H, H7a or H7b), 2.92 (m, 1H, H6), 3.20 (s, 3H, NCH3), 3.49 (t, 2H, H8, H8, J=6 Hz), 6.62 (s, 1H, H3), 7.46 (q, 1H, H5, JH5 --CF3 =~1.5 Hz), 9.40 (broad s, 1H,NH).

Workup

  1. filtrationof ether, filtered
  2. washwashed with more ether, 1.3 g
  3. customm.p. 225°-230°, wet 200°

Sources & evidence

ORD record
ord-2c25b890967c4f64905930cb63d0f4fa
Source dataset
uspto-grants-1980_05
Patent number
US04202981

Reaction notes

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