2-Chloro-5-nitrobenzoic acid → 5-Nitro-2-(pyrrolidin-1-yl)benzoic acid

HRID 1833300Notes

Reaction equation

HRID 1833300 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>>[N+:11]([C:8]1[CH:9]=[CH:10][C:2]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 172872-Chloro-5-nitrobenzoic acidHCID 31268Pyrrolidine

Product 1

HCID 27257545-Nitro-2-(pyrrolidin-1-yl)benzoic acid

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.

Workup

  1. customA cooling bath was applied
  2. additionas necessary during the addition
  3. additionAfter the addition
  4. temperaturethe reaction was heated on a steam bath for three hours
  5. temperaturecooled
  6. custommade acidic with concentrated HCl until precipitation of product
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-530964d6ae4f43208fecdabae5825fa9
Source dataset
uspto-grants-1978_01
Patent number
US04066457

Reaction notes

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