Methanol → 5-[5-(N-acetyl-anilino)-2, 3-pentadienylidene]-2,7-diphenyl-4-methylpyrazolo[3,4-b]pyridine-3,6-dione

HRID 1073047Notes

Reaction equation

HRID 1073047 reaction equation
CO.[C:3]1([N:9]2[C:17](=[O:18])[C:16]3[C:15]([CH3:19])=[CH:14][C:13](=[O:20])[N:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:11]=3[NH:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.C1(N=[CH:35][CH:36]=[CH:37][CH:38]=[CH:39][NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)C=CC=CC=1.[C:47](OC(=O)C)(=[O:49])[CH3:48]>C(N(CC)CC)C>[C:47]([N:40]([CH2:39][CH:38]=[C:37]=[CH:36][CH:35]=[C:14]1[C:13](=[O:20])[N:12]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:11]2=[N:10][N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:17](=[O:18])[C:16]2=[C:15]1[CH3:19])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)(=[O:49])[CH3:48]

Participants

6

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 73902N-(5-(phenylamino)penta-2,5-dienylidene)aniline monohydrochlorideHCID 3603164-methyl-2,7-diphenyl-1H-pyrazolo[3,4-b]pyridine-3,6-dione

Product 1

HCID 571236985-[5-(N-acetyl-anilino)-2, 3-pentadienylidene]-2,7-diphenyl-4-methylpyrazolo[3,4-b]pyridine-3,6-dione

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a solution prepared by adding methanol (50 ml) and triethylamine (2.8 ml) to 2,7-diphenyl-4-methylpyrazolo(3,4-b) pyridine-3,6-dione (3.17 g), 1,7-diphenyl-1,7-diaza-1,3,5-heptatriene hydrochloride (2.85 g) was dissolved and then acetic anhydride (1.88 ml) was added, and the mixture was stirred at room temperature for one hour. The resulting precipitate was collected by filtration, washed with methanol and dried to obtain 5-[5-(N-acetylanilino)-2,3-pentadienylidene]-2,7-diphenyl-4-methylpyrazolo(3,4-b)pyridin-3, 6-dione (1.9). To these crystals (1.5 g), N,N-dimethylformamide (60 ml), 2,7-diphenyl-4-methylpyrazolo(3,4-b)pyridin-3,6-dione (0.95 g) and triethylamine (0.42 g) were added, and stirred at 50° C. for 2 hours. After a trace amount of insoluble matters were removed by filtration, ethyl acetate of 10-fold the volume of the filtrate was added thereto while stirring for crystallization. The resulting crystals were redissolved in a small amount of N,N-dimethylformamide, and a 10-fold volume of ethyl acetate was added thereto for crystallization. The resulting crystals were collected by filtration and dried to obtain compound II-2 (1.3 g). Gold crystals, melting point 300° C. or more, λmaxDMF 792 nm

Workup

  1. customIn a solution prepared
  2. dissolutionwas dissolved
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-5d4fb42d68014090b545eac1426edc4c
Source dataset
uspto-grants-1990_11
Patent number
US04968593

Reaction notes

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