Hydrazine hydrate (1:1) → HCID 136385215, compound

HRID 1967979Notes

Reaction equation

HRID 1967979 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]1[CH:16]([C:17]2[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=2)[C:15](=O)[C:14]2[C:13]([C:24](OCC)=[O:25])=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8]1.O.[NH2:30][NH2:31]>CO>[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]1[NH:8][C:9]2[C:14]3[C:15](=[N:30][NH:31][C:24](=[O:25])[C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:16]1[C:17]1[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67258792HCID 67258792, compound

Product 1

HCID 136385215HCID 136385215, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2,3-bis(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (120 mg) in 85% hydrazine monohydrate (2 mL) and methanol (3 mL) was stirred at room temperature for 3.5 h. Evaporated the solvent and methanol (1 mL) was added, filtered and washed the cake by methanol (2 mL) to obtain a white solid. The solid was dried in vacuum at 50° C. to obtain 8,9-bis(1-methyl-1H-imidazol-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (45 mg, yield 41%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 3.46 (s, 3H), 3.49 (s, 3H), 4.78-4.81 (d, J=12.0 Hz, 1H), 5.08-5.11 (d, J=12.0 Hz, 1H), 6.69 (s, 1H), 6.76-6.79 (m, 3H), 6.99-7.02 (d, J=7.6 Hz, 1H), 7.42-7.49 (m, 2H); LC-MS (ESI) m/z: 348 (M+1)+.

Workup

  1. customEvaporated the solvent and methanol (1 mL)
  2. additionwas added
  3. filtrationfiltered
  4. washwashed the cake by methanol (2 mL)
  5. customto obtain a white solid
  6. customThe solid was dried in vacuum at 50° C.

Sources & evidence

ORD record
ord-dc263b67b24a4a3eb0d575209dc05496
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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