Ethylamine → N-Ethyl-3-nitro PABA

HRID 2121937Notes

Reaction equation

HRID 2121937 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14]([NH2:16])[CH3:15]>>[CH2:14]([NH:16][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12])[CH3:15]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 3729086N-Ethyl-3-nitro PABA

Procedure

In a manner similar to Example 31, 4-fluoro-3-nitrobenzoic acid was treated with ethylamine to give 4-ethylamino-3-nitrobenzoic acid, which was then esterified with anhydrous hydrogen chloride in methanol to give the title compound. 1H-NMR (CDCl3): δ 8.89 (1H, d), 8.28 (1H, br s), 8.06 (1H, dd), 6.87 (1H, d), 3.90 (3H, s), 3.42 (2H, m), 1.40 (3H, t).

Sources & evidence

ORD record
ord-784a810c71914ebda0a9dd97bb3c2711
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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