Hydrazine → HCID 135988232, compound

HRID 1723832Notes

Reaction equation

HRID 1723832 reaction equation
[C:1]([C:4]1[C:5](=[O:19])[NH:6][C:7]2[C:12]([C:13]=1O)=[CH:11][C:10]1[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=1[CH:8]=2)(=O)[CH3:2].[NH2:20][NH2:21]>Cl.CC(N(C)C)=O>[CH3:2][C:1]1[NH:20][N:21]=[C:13]2[C:12]3[CH:11]=[C:10]4[CH:15]=[CH:16][CH:17]=[CH:18][C:9]4=[CH:8][C:7]=3[NH:6][C:5](=[O:19])[C:4]=12

Participants

5

Reactant 2

HCID 9321HydrazineHCID 57559684HCID 57559684, compound

Product 1

HCID 135988232HCID 135988232, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-acetyl-4-hydroxybenzo[g]quinolin-2(1H)-one (1-4) (3.95 g, 15.6 mmol, 1.0 equiv), hydrazine (0.74 ml, 0.75 g, 23.4 mmol, 1.5 equiv), and catalytic conc. HCl (2 drops) in DMA (30 ml) were heated to 140° C. under nitrogen for 55 hours. The solution was cooled and the solid precipitate was filtered, washed with methanol (100 ml×3), and dried to yield 3-methyl-2,5-dihydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-5) as a tan solid. 1H NMR (500 MHz, DMSO-d6)) δ 11.14 (s, 1H), 8.61 (s, 1H), 7.97 (d, 1H, J=8.0 Hz) 7.85 (d, 1H, J=8.5 Hz), 7.70 (s, 1H), 7.50 (m, 1H), 7.41 (m, 1H), 2.59 (s, 3H). LRMS m/z/z (M+H) 250.2 found, 250.1 required.

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe solid precipitate was filtered
  3. washwashed with methanol (100 ml×3)
  4. customdried

Sources & evidence

ORD record
ord-0d397a37340442f8800d89561b8a238d
Source dataset
uspto-grants-2009_02
Patent number
US07485649B2

Reaction notes

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