5-Nitro-2-(pyrrolidin-1-yl)benzoic acid → HCID 609825, compound
Reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
20.1 Grams 2-chloro-5-nitrobenzoic acid was added in portions to 100 ml pyrrolidine. A cooling bath was applied as necessary during the addition. After the addition was complete, the reaction was heated on a steam bath for three hours, cooled, poured into ice water and made acidic with concentrated HCl until precipitation of product was complete. Recrystallization from ethanol gave 19.4 grams 5-nitro-2-(1-pyrrolidinyl)benzoic acid. m.p. = 224°-266° C dec. The nitro compound was reduced catalytically in ethanol with 5% palladium on carbon catalyst to give 5-amino-2-(1-pyrrolidinyl)benzoic acid. m.p. = 205°-208° C dec.
Sources & evidence
- ORD record
- ord-e05ebbeaeb3f47d08597ea37fc2e7839
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04066457
Reaction notes
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