Quinoline, 4-chloro-, 1-oxide → HCID 178440351, compound

HRID 1987606Notes

Reaction equation

HRID 1987606 reaction equation
[CH:1]([C:4]1[CH2:8][C:7](=[O:9])[NH:6][N:5]=1)([CH3:3])[CH3:2].[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N+:14]([O-])=[CH:13][CH:12]=1>C(OC(=O)C)(=O)C>[Cl:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14]/[C:13](=[C:8]2/[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][NH:6][C:7]/2=[O:9])/[CH:12]=1

Participants

4

Reactant 2

HCID 3741098Quinoline, 4-chloro-, 1-oxideHCID 184394413-isopropyl-1H-pyrazol-5(4H)-one

Product 1

HCID 178440351HCID 178440351, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Methyl isobutyrylacetate (0.5 g, 3.47 mmol) was stirred in ethanol and acetic acid (10:1, 2:0.2 mL) and treated with hydrazine (0.13 mL, 4.16 mmol). After 24 hrs, the resulting solid was filtered off and washed with a minimum amount of ethanol to yield 3-isopropyl-1H-pyrazol-5(4H)-one. Then, the 3-isopropyl-1H-pyrazol-5(4H)-one (0.169 g, 1.34 mmol) and 4-chloroquinoline N-oxide (0.24 g, 1.34 mmol) were stirred in acetic anhydride (1.5 mL) at ambient temperature for 20-30 minutes. The reaction mixture was concentrated and the resulting solid was filtered off and washed with a minimum amount of ether to yield Example 18. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (d, J=6.82 Hz, 6H) 3.98 (bs, 1H) 7.61 (t, J=7.58 Hz, 1H) 7.76-7.82 (m, 1H) 7.93 (d, J=8.34 Hz, 1H) 8.08-8.18 (m, 2H); ESI-MS: m/z calc'd for C15H14ClN3O 287.74. found 288.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationthe resulting solid was filtered off
  3. washwashed with a minimum amount of ether
  4. customto yield Example 18

Sources & evidence

ORD record
ord-d932e92794db482ea0d5114db2315d4d
Source dataset
uspto-grants-2009_06
Patent number
US07550598B2

Reaction notes

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