4-Methylmorpholine → 4'-Methyl-[1,1'-biphenyl]-4-carbohydrazide

HRID 923590Notes

Reaction equation

HRID 923590 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:32][NH2:33].C([O-])(O)=O.[Na+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:32][NH2:33])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 9321HydrazineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 20634214'-Methyl-4-biphenylcarboxylic acid

Product 1

HCID 13935694'-Methyl-[1,1'-biphenyl]-4-carbohydrazideYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of 4′-methyl-[1,1′-biphenyl]-4-carboxylic acid (240 mg, 1.13 mmol) and 4-methylmorpholine (131 μL, 1.19 mmol) in THF (3 mL) was added isobutyl chloroformate (147 μL, 1.13 mmol). After 1 h the reaction mixture was added through a syringe filter to a stirring solution of hydrazine (1.24 mL, 1.24 mmol, 1 M in THF) in THF (1 mL). After stirring a further 30 min at room temperature, the reaction mixture was poured into NaHCO3 (20 mL) and extracted with DCM (3×20 mL). The combined organic extracts were dried over MgSO4 and evaporated. The crude product was purified by column chromatography (MeOH/DCM) to give 152 mg (59%) of 4′-methyl-[1,1′-biphenyl]-4-carbohydrazide INT-50 as a white solid. LCMS-ESI (m/z) calculated for C14H14N2O: 226; found 227 [M+H]+, tR=1.62 min (Method 10).

Workup

  1. additionAfter 1 h the reaction mixture was added through a syringe
  2. extractionextracted with DCM (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customevaporated
  5. customThe crude product was purified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-4e7454fdb5cc4af09600c42c104aa31e
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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