Hydrazine hydrate (1:1) → 5-(3-Chlorophenylamino)benzo[c][2,6]naphthyridine-7-carbohydrazide

HRID 1919687Notes

Reaction equation

HRID 1919687 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[C:12]3=[CH:19][CH:20]=[CH:21][C:22]([C:23](OC)=[O:24])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.O.[NH2:28][NH2:29]>CN(C=O)C.CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[C:12]3=[CH:19][CH:20]=[CH:21][C:22]([C:23]([NH:28][NH2:29])=[O:24])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57395611Methyl 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carboxylate

Product 1

HCID 575006985-(3-Chlorophenylamino)benzo[c][2,6]naphthyridine-7-carbohydrazideYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carboxylate (47 mg) was mixed with Methanol (1 ml) and Hydrazine hydrate (1 ml). 2-3 drops of DMF were added and the mixture was stirred at 60° C. for 2 hours. The volatiles were removed and another amount of reagent Methanol (1 ml) and Hydrazine (1 ml) were added, and the mixture was stirred at 60° C. for an extra 2 hours. The volatiles were removed in vacuo and the material was crashed out using AcOEt/hexanes. Filtration and drying afforded 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carbohydrazide as a solid (29 mg, 62% yield). LCMS (ES): >85% pure, m/z 364 [M+1]+.

Workup

  1. customThe volatiles were removed
  2. additionanother amount of reagent Methanol (1 ml) and Hydrazine (1 ml) were added
  3. stirringthe mixture was stirred at 60° C. for an extra 2 hours
  4. customThe volatiles were removed in vacuo
  5. filtrationFiltration
  6. customdrying

Sources & evidence

ORD record
ord-438c5a8454bf4c89bba80b429dbe793a
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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