Methanol → HCID 22010563, compound

HRID 323141Notes

Reaction equation

HRID 323141 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:47]=[CH:46][C:20]([C:21]([N:23]([CH3:45])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][N:34]4C(=O)C5=CC=CC=C5C4=O)=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.O.NN.CO>C(O)C.C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([N:23]([CH3:45])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH2:31][CH2:32][CH2:33][NH2:34])=[O:22])=[CH:46][CH:47]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 22010892HCID 22010892, compound

Product 1

HCID 22010563HCID 22010563, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-phthalimidopropyloxy)phenyl]benzamide (545 mg) and hydrazine hydrate (0.212 ml) in ethanol (20 ml) was refluxed for 4 hours. After removal of insoluble material, the filtrate was evaporated in vacuo to give an oil and the oil was subjected to a silica gel column (5% methanol in chloroform) to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(3-aminopropyloxy)phenyl]benzamide (425 mg).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customAfter removal of insoluble material
  3. customthe filtrate was evaporated in vacuo
  4. customto give an oil

Sources & evidence

ORD record
ord-380f2ee1c30f42aab2fd6148563789f2
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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