Hydrochloric Acid → 2-Morpholino-5-nitrobenzoic acid

HRID 1833298Notes

Reaction equation

HRID 1833298 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[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.Cl>>[O:17]1[CH2:18][CH2:19][N:14]([C:2]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:15][CH2:16]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 27257552-Morpholino-5-nitrobenzoic acid

Procedure

20.1 Grams 2-chloro-5-nitrobenzoic acid was added in portions to 87 ml morpholine. The temperature of the thick mixture rose to 75° C. After being stirred at reflux temperature for five hours, the mixture was poured into ice water, made acidic with concentrated HCl, filtered, dried and recrystallized from ethanol to give 20.3 grams 2-morpholino-5-nitrobenzoic acid. m.p. = 168°-170° C. The nitro compound was reduced catalytically in ethanol-water (3:1) with 5% palladium on carbon catalyst to give 5-amino-2-morpholinobenzoic acid. m.p. = 307°-308° C.

Workup

  1. customrose to 75° C
  2. temperatureat reflux temperature for five hours
  3. filtrationfiltered
  4. customdried
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6cae31790beb4aae9198584e739a5d71
Source dataset
uspto-grants-1978_01
Patent number
US04066457

Reaction notes

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