Hydrazine → HCID 135999903, compound

HRID 1986895Notes

Reaction equation

HRID 1986895 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[CH2:15][CH2:16][CH2:17][CH2:18][C:9]=1[CH:8]=2)(=O)[CH3:2].[NH2:20][NH2:21]>Cl.CC(N(C)C)=O.O>[CH3:2][C:1]1[NH:20][N:21]=[C:13]2[C:12]3[CH:11]=[C:10]4[CH2:15][CH2:16][CH2:17][CH2:18][C:9]4=[CH:8][C:7]=3[NH:6][C:5](=[O:19])[C:4]=12

Participants

6

Reactant 2

HCID 9321HydrazineHCID 57722728HCID 57722728, compound

Product 1

HCID 135999903HCID 135999903, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-acetyl-4-hydroxy-6,7,8,9-tetrahydrobenzo[g]quinolin-2(1H)-one (1-5) (2.0 g, 7.8 mmol, 1 equiv), hydrazine (0.40 mL, 0.41 g, 13 mmol, 1.6 equiv), and catalytic concentrated hydrochloric acid solution (2 drops) in DMA (30 mL) was heated at 140° C. under nitrogen for 16 h. The solution was cooled and diluted with water (30 mL). The precipitate was filtered, washed with hexanes (3×100 mL), and dried to yield 3-methyl-2,5,7,8,9,10-hexahydro-4H-benzo[g]pyrazolo[4,3-c]quinolin-4-one (1-6) as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ 13.51 (s, 1H), 10.99 (s, 1H), 7.70 (s, 1H) 7.04 (s, 1H), 2.78 (m, 4H), 2.59 (s, 3H), 1.76 (m, 4H). LRMS m/z (M+H) 254.4 found, 254.1 required.

Workup

  1. temperatureThe solution was cooled
  2. filtrationThe precipitate was filtered
  3. washwashed with hexanes (3×100 mL)
  4. customdried

Sources & evidence

ORD record
ord-1dd1ba707480494a8811abf303946b9e
Source dataset
uspto-grants-2009_06
Patent number
US07550477B2

Reaction notes

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