2,8-Diacetylamino-1-tetralone → 3-Acetylamino-5-amino-8-methyl-2,3-dihydroquinoline-4-one

HRID 355960Notes

Reaction equation

HRID 355960 reaction equation
C([N:4]1[C:13]2[C:8](=[C:9]([NH:15]C(=O)C)[CH:10]=[CH:11][C:12]=2[CH3:14])[C:7](=[O:19])[CH:6]([NH:20][C:21](=[O:23])[CH3:22])[CH2:5]1)(=O)C.C(NC1CCC2C(=C(NC(=O)C)C=CC=2)C1=O)(=O)C>>[C:21]([NH:20][CH:6]1[C:7](=[O:19])[C:8]2[C:13](=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[NH2:15])[NH:4][CH2:5]1)(=[O:23])[CH3:22]

Participants

3

Reactant 2

HCID 120472982,8-Diacetylamino-1-tetraloneHCID 224494801-Acetyl-3,5-diacetylamino-8-methyl-2,3-dihydro-quinoline-4-one

Product 1

HCID 224494723-Acetylamino-5-amino-8-methyl-2,3-dihydroquinoline-4-one

Procedure

The procedure of Example 1-(4) was followed by using 1.40 gm of the compound prepared in (3) above instead of 2,8-diacetylamino-1-tetralone. The reaction product was post-treated to obtain 0.79 gm of the title compound. NMR(CDCl3)δ: 2.01(s, 3H), 2.08(s, 3H), 3.0-4.5(m, 3H), 5.89(d, 1H, J=8 Hz), 6.95(d, 1H, J=8 Hz) 5.7-6.8(br.s, 2H); MASS m/z: 233(M+)

Workup

  1. additionThe reaction product was post-treated

Sources & evidence

ORD record
ord-340be32089cc4e189c2f2e36be24c3e6
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

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