Hydrazine hydrate (1:1) → HCID 135924304, compound

HRID 1967976Notes

Reaction equation

HRID 1967976 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:15](=O)[C:14]2[C:13]([C:24]([O:26]C)=O)=[CH:12][CH:11]=[CH:10][C:9]=2[NH:8]1.CN1C=CN=C1C1C(C2C=CC=CC=2)C(=O)C2C(C(OCC)=O)=CC=CC=2N1.O.[NH2:57][NH2:58]>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:57][NH:58][C:24](=[O:26])[C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:16]1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 67261602HCID 67261602, compoundHCID 67261769HCID 67261769, compound

Product 1

HCID 135924304HCID 135924304, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(1-methyl-1H-imidazol-2-yl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 2-(1-methyl-1H-imidazol-2-yl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (87 mg) in 85% hydrazine monohydrate (4 mL) and methanol (10 mL) was stirred at room temperature for overnight. The mixture was extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give the crude. The crude product was purified by pre-HPLC to give 8-(1-methyl-1H-imidazol-2-yl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (34 mg, yield 42%) as a yellow solid. 1H-NMR (400 MHz, CD3OD) δ (ppm): 3.41 (s, 3H), 4.49 (d, 1H), 5.35 (d, 1H), 7.18-7.20 (m, 2H), 7.26-7.29 (m, 1H), 7.33-7.35 (m, 3H), 7.40 (d, 1H), 7.61 (d, 1H), 7.71-7.75 (m, 2H); LC-MS (ESI) m/z: 344 (M+1)+.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (50 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customto give the crude
  6. customThe crude product was purified by pre-HPLC

Sources & evidence

ORD record
ord-3f2f4bafb0db4aa0800515190aa902a7
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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