Triethylamine → 4-methoxybenzoic acid N'-(4-amino-3-nitrobenzoyl)-hydrazide
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:35][O:36][C:37]1[CH:46]=[CH:45][C:40]([C:41]([NH:43][NH2:44])=[O:42])=[CH:39][CH:38]=1.CCN(CC)CC>CN(C=O)C.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:44][NH:43][C:41](=[O:42])[C:40]2[CH:45]=[CH:46][C:37]([O:36][CH3:35])=[CH:38][CH:39]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 4-amino-3-nitrobenzoic acid (3.64 g, 20 mmol) in DMF (50 mL) was added HOBT (2.70 g, 20 mmol) and EDCI (3.83 g, 20 mmol). After the addition, the solution was stirred at 25° C. for 10 min then 4-methoxybenzoic acid hydrazide (3.32 g, 20 mmol) was added and followed by the addition of NEt3 (8.35 mL, 60 mmol). The solution was stirred at 25° C. overnight and water was added. The resulting suspension was filtered and the solid was washed with water. The yellow solid was dried under reduced pressure and was purified by flash chromatography (heptane/EtOAc=1:3) to give the title compound. MS: m/z 331 (M+1).
Workup
- additionAfter the addition
- stirringThe solution was stirred at 25° C. overnight
- filtrationThe resulting suspension was filtered
- washthe solid was washed with water
- customThe yellow solid was dried under reduced pressure
- customwas purified by flash chromatography (heptane/EtOAc=1:3)
Sources & evidence
- ORD record
- ord-50483ee32d0144b7a36b1a2792a9e3b3
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879850B2
Reaction notes
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