3-Amino-4-methylbenzohydrazide → HCID 68289152, compound

HRID 541418Notes

Reaction equation

HRID 541418 reaction equation
CO[C:3]1[CH2:4][CH:5]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)[CH2:6][CH2:7][N:8]=1.[NH2:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=1[CH3:28])[C:21]([NH:23][NH2:24])=O>ClC1C=CC=CC=1Cl>[NH2:17][C:18]1[CH:19]=[C:20]([C:21]2[N:8]3[CH2:7][CH2:6][CH:5]([C:9]4[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=4)[CH2:4][C:3]3=[N:24][N:23]=2)[CH:25]=[CH:26][C:27]=1[CH3:28]

Participants

4

Reactant 2

HCID 185260563-Amino-4-methylbenzohydrazide2×HCID 68289109HCID 68289109, compound2×

Product 1

HCID 68289152HCID 68289152, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4-(6-methoxy-2,3,4,5-tetrahydropyridin-4-yl)benzonitrile (compound 347.3, 5.00 g, 23.36 mmol, 1.00 equiv) in 1,2-dichlorobenzene (100 mL) was added 3-amino-4-methylbenzohydrazide (compound 347.4, 4.63 g, 28.0 mmol, 1.20 equiv). The resulting solution was stirred overnight at 150° C. in an oil bath. After cooling to ambient temperature, the resulting mixture was purified using silica gel column chromatography with dichloromethane/methanol (1:0˜100:1) as eluent to furnish 2.40 g (31%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe resulting mixture was purified

Sources & evidence

ORD record
ord-43d5a2cfea374db9918d08cf41ca8fb8
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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