Acetic Acid → 4-(ethylamino)benzoic acid
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[BH4-].[Na+].[C:13](O)(=O)[CH3:14].O>C(#N)C>[CH2:13]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)[CH3:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A mixture composed of 4-aminobenzoic acid (30 g), sodium borohydride (32.3 g) and acetic acid (550 cc) is left stirring for 26 hours at 25° C. The reaction mixture is then concentrated to dryness at 70° C. under reduced pressure (4 kPa). The product obtained is treated with distilled water (2000 cc) and the precipitate formed is separated by filtration, washed with distilled water (20 cc) and dried in the air. The product obtained is dissolved in boiling acetonitrile (250 cc). After 2 hours' cooling at 25° C., the crystallized solid is separated by filtration, washed with acetonitrile (10 cc) and dried at 40° C. under reduced pressure (0.07 kPa). 4-Ethylaminobenzoic acid (18 g), m.p. 174° C., is obtained.
Workup
- waitis left
- concentrationThe reaction mixture is then concentrated to dryness at 70° C. under reduced pressure (4 kPa)
- customThe product obtained
- customthe precipitate formed
- customis separated by filtration
- washwashed with distilled water (20 cc)
- customdried in the air
- customThe product obtained
- dissolutionis dissolved
- temperatureAfter 2 hours' cooling at 25° C.
- customthe crystallized solid is separated by filtration
- washwashed with acetonitrile (10 cc)
- customdried at 40° C. under reduced pressure (0.07 kPa)
Sources & evidence
- ORD record
- ord-db05bfab8e83434ca921c553af68763b
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04753933
Reaction notes
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