Diisopropylethylamine → 6-(4-Benzyloxyphenylamino)-5-nitronicotinic acid methyl ester

HRID 499053Notes

Reaction equation

HRID 499053 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7](Cl)=[N:6][CH:5]=1.Cl.[CH2:16]([O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(C(C)C)C(C)C>CO>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([NH:28][C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:30][CH:29]=2)=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 346961Methyl 6-chloro-5-nitronicotinateHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 598156466-(4-Benzyloxyphenylamino)-5-nitronicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-chloro-5-nitro-nicotinic acid methyl ester (216 mg, 1.0 mmol) and 4-benzyloxyaniline hydrochloride (280 mg, 1.2 mmol) in MeOH (10 mL) was added iPr2NEt (0.35 mL, 2.0 mmol). The resulting mixture was stirred at rt overnight, a red solid precipitated from the mixture, which was collected by filtration. MS (ES, Pos.): m/z 380 [MH+]. 1H NMR (CDCl3, 400 MHz): δ=3.94 (s, 3H), 5.10 (s, 2H), 7.03 (d, J=8.8 Hz, 2H), 7.38-7.46 (m, 5H), 7.50 (d, J=8.8 Hz, 2H), 9.01 (d, J=2.0 Hz, 1H), 9.08 (d, J=2.0 Hz, 1H), 10.2 (br s, 1H).

Workup

  1. customa red solid precipitated from the mixture, which
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-3fcabf7d32194619b0c6fc1df3fe46c4
Source dataset
uspto-grants-2010_08
Patent number
US07767673B2

Reaction notes

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