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

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].[CH2:15]([NH2:17])[CH3:16]>>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([NH:17][CH2:15][CH3:16])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

Reactant 2

HCID 6341Ethylamine

HCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

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

Procedure

4-Ethylamino-3-nitro-benzoic acid methyl ester (4.0 g) was prepared by following General Procedure A starting from methyl 4-chloro-3-nitrobenzoate (5.0 g) in ethylamine (2.0 M in THF, 50 mL). The crude product was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record: ord-a3a1c21ff16f4d7c9e6cc1b5dd465180
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759535B2

Reaction notes

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