1,3-Cyclohexanedione, 4,4-dimethyl- → 4-(4-bromo-3-chlorophenyl)-1,6,6-trimethyl-4,7,8,9-tetrahydro-1H-pyrazolo[3,4-b]quinoline-3,5(2H,6H)-dione

Participants

Role	Name	HCID	Charge
Reactant	1,3-Cyclohexanedione, 4,4-dimethyl-	HCID 136360	—
Reactant	5-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one	HCID 252198	—
Reactant	4-Bromo-3-chlorobenzaldehyde	HCID 14049806	—
Product	4-(4-bromo-3-chlorophenyl)-1,6,6-trimethyl-4,7,8,9-tetrahydro-1H-pyrazolo[3,4-b]quinoline-3,5(2H,6H)-dione	HCID 10274739	67.2%

Reaction Steps

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.08 g, 0.75 mmol), 3-chloro-4-bromobenzaldehyde (0.13 g, 0.75 mmol) from Example 40C, and 4,4-dimethyl-1,3-cyclohexanedione (0.10 g, 0.75 mmol) were processed as described in Example 22 to provide the title compound (0.22 g, 67%). 1H NMR (DMSO-d6) δ 0.92 (s, 3H), 0.98 (s, 3H), 1.78 (t, 2H), 2.55 (m, 2H), 3.47 (s, 3H), 4.81 (s, 1H), 7.0 (dd, 1H), 7.29 (d, 1H), 7.55 (d, 1H), 9.52 (bs, 1H), 9.67 (s, 1H); MS (ESI−) m/z 436 (M−H)−; Anal. Calcd for C19H19N3BrClO2: C, 52.23; H, 4.35; N, 9.62. Found: C, 52.35; H, 4.24; N, 9.62.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06780872B2
Source dataset	uspto-grants-2004_08
ORD ID	ord-acb1de264a5845efb88be055db4d06c2
Source note	uspto-grants-2004_08