Hydrazine hydrate (1:1) → HCID 136385259, compound

HRID 907879Notes

Reaction equation

HRID 907879 reaction equation
O=[C:2]1[C:11]2[C:10]([C:12]([O:14]C)=O)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O.[NH2:29][NH2:30]>>[C:22]1([CH:3]2[C:2]3=[N:29][NH:30][C:12](=[O:14])[C:10]4[CH:9]=[CH:8][CH:7]=[C:6]([C:11]=43)[NH:5][CH:4]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67261305HCID 67261305, compound

Product 1

HCID 136385259HCID 136385259, compoundYield 37%

Procedure

A mixture of methyl 4-oxo-3-phenyl-2-(pyridin-2-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (30 mg, 0.08 mmol) and hydrazine monohydrate (1 mL) was stirred at room temperature for 3 h. The resulting mixture was evaporated under reduced pressure to 10 mL and then filtered, 10 mg of 9-phenyl-8-(pyridin-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one was obtained, yield 37%. 1H-NMR (400 MHz, CDCl3) δ (ppm): 4.60 (d, 1H), 4.86-4.88 (m, 1H), 5.21 (s, 1H), 6.96 (dd, 1H), 7.08-7.17 (m, 4H), 7.22-7.28 (m, 3H), 7.46-7.49 (m, 1H), 7.60 (t, 1H), 7.73 (dd, 1H), 8.59 (d, 1H), 9.77 (s, 1H); LC-MS (ESI) m/z: 341 (M+1)+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure to 10 mL
  2. filtrationfiltered

Sources & evidence

ORD record
ord-79ee2a977595446aa86064ee841b37dc
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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