Hydrazine hydrate (1:1) → HCID 136186303, compound

HRID 1968049Notes

Reaction equation

HRID 1968049 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]1[C:16](=O)[C:15]2[C:14]([C:18]([O:20]CC)=O)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][CH:8]1[C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1.O.[NH2:34][NH2:35]>CO>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]1[C:16]2=[N:34][NH:35][C:18](=[O:20])[C:14]3[CH:13]=[CH:12][CH:11]=[C:10]([C:15]=32)[NH:9][CH:8]1[C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260485Ethyl 1,2,3,4-tetrahydro-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-2-[4-(trifluoromethyl)phenyl]-5-quinolinecarboxylate

Product 1

HCID 136186303HCID 136186303, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-(1-methyl-1H-imidazol-2-yl)-4-oxo-2-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (150 mg, 0.34 mmol) in 85% hydrazine monohydrate (4 ml) and methanol (6 mL) was stirred at room temperature for 2 h. The mixture was filtered and washed with water to give the title compound (25 mg, yield: 18%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.46 (s, 3H), 4.81 (d, J=10.8 Hz, 1H), 5.07 (d, J=10.8 Hz, 1H), 6.82 (s, 1H), 6.97 (d, 1H), 7.16 (d, J=8 Hz, 1H), 7.41 (d, J=7.6 Hz, 2H), 7.58-7.69 (m, 5H), 12.22 (d, 1H); LC-MS (ESI) m/z: 412 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-5ba2ee5c73904ecd8d9b39977231599f
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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