Hydrazine hydrate (1:1) → HCID 178488917, compound

HRID 1526128Notes

Reaction equation

HRID 1526128 reaction equation
O.[NH2:2][NH2:3].[OH:4][N:5]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12]2[C:11]([C:19]#[N:20])=[C:10](SC)[N:9]=[C:8]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[C:7]=2[C:6]1=[O:31]>C(O)CCC.CS(C)=O>[NH2:20][C:19]1[C:11]2[C:12]3[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[N:5]([OH:4])[C:6](=[O:31])[C:7]=3[C:8]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[N:9][C:10]=2[NH:3][N:2]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70874059HCID 70874059, compound

Product 1

HCID 178488917HCID 178488917, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

37.4 ml (770 mmol) of hydrazine hydrate is added to a solution of 3 g (7.7 mmol) of 6-hydroxy-4-(4-methoxyphenyl)-2-(methylthio)-5-oxo-5,6-dihydrobenzo[c][2,7]-naphthyridine-1-carbonitrile dissolved in 80 ml of butan-1-ol and 32 ml of dimethylsulfoxide. The reaction medium is carried at 150° C. for 3 hours and then is allowed to rest at room temperature overnight. The precipitate obtained is filtered and then rinsed with methanol to yield 1.14 g (39%) of 1-amino-7-hydroxy-5-(4-methoxyphenyl)-3H-benzo[f]pyrazolo[3,4-c][2,7]naphthyridin-6(7H)-one in the form of a yellow solid.

Workup

  1. waitto rest at room temperature overnight
  2. customThe precipitate obtained
  3. filtrationis filtered
  4. washrinsed with methanol

Sources & evidence

ORD record
ord-2977865368ce4b579ddcff8bd6e9f9fc
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

Loading…