Ethylamine hydrochloride → Methyl 4-(ethylamino)-3-nitrobenzoate

HRID 410926Notes

Reaction equation

HRID 410926 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][CH2:16][N:17](C(C)C)C(C)C.Cl.C(N)C>CN(C=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([NH:17][CH2:16][CH3:15])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

5

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 20626654Methyl 4-(ethylamino)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Ethylamino-3-nitro-benzoic acid methyl ester (8.3 g) was prepared by following General Procedure A starting from methyl 4-chloro-3-nitrobenzoate (10.0 g), DIEA (1.6 mL) and ethylamine hydrochloride salt (4.5 g) in DMF (50.0 mL). The crude product was used in the next step without further purification.

Workup

  1. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-50fa9306b5db42fbb3074b43b35594d7
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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