Hydrazine hydrate (1:1) → HCID 57500680, compound

HRID 1919659Notes

Reaction equation

HRID 1919659 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][C:21]([C:23](OC)=[O:24])=[CH:22][C:11]=3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.O.[NH2:28][NH2:29]>CO.CN(C=O)C>[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][C:21]([C:23]([NH:28][NH2:29])=[O:24])=[CH:22][C:11]=3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 50942535HCID 50942535, compound

Product 1

HCID 57500680HCID 57500680, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-8-carboxylate (47 mg, 0129 mmol) was suspended in a mixture of methanol (1 ml) and hydrazine hydrate (1 ml). 3 drops of DMF were added and the mixture stirred at 60-70° C. for 2 hours. The volatiles were removed in vacuo. The resulting material was suspended in AcOEt/Hexanes, filtered and dried to afford 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-8-carbohydrazide as solid (47 mg, 100% yield). LCMS (ES): 95% pure, m/z 364 [M+1]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-dcf78788e20f42fc8649dcc8a6ac72fc
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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