Hydrazine hydrate (1:1) → 8-phenyl-9-(thiazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one

HRID 1967971Notes

Reaction equation

HRID 1967971 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][CH:17]=2)[CH:3]1[C:22]1[S:26][CH:25]=[N:24][CH:23]=1.O.[NH2:28][NH2:29]>CO>[C:16]1([CH:4]2[NH:5][C:6]3[C:11]4[C:2](=[N:28][NH:29][C:12](=[O:14])[C:10]=4[CH:9]=[CH:8][CH:7]=3)[CH:3]2[C:22]2[S:26][CH:25]=[N:24][CH:23]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67258775Methyl 4-oxo-2-phenyl-3-(thiazol-5-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate

Product 1

HCID 1363851638-phenyl-9-(thiazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-oneYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-oxo-2-phenyl-3-(thiazol-5-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (110 mg, 0.29 mmol) and hydrazine monohydrate (2 mL) were added to methanol (10 mL) and the mixture was stirred room temperature for 4 h. The resulting mixture was evaporated under reduced pressure to 10 mL and then filtered; the filtrate was concentrated to give 8-phenyl-9-(thiazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (13 mg, yield 13%) as a white solid. 1H-NMR (400 MHz, CD3OD) δ (ppm): 4.67 (d, 1H), 4.78 (d, 1H), 7.10-7.19 (m, 4H), 7.24 (t, 2H), 7.45-7.56 (m, 2H), 8.76 (s, 1H); LC-MS (ESI) m/z: 347 (M+1)+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure to 10 mL
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b3a33b3d174742688620a0609d499d83
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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