Ammonia → HCID 89739572, compound

HRID 925406Notes

Reaction equation

HRID 925406 reaction equation
[NH3:1].Br[CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=[O:8]>C(O)C>[NH2:1][CH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 204936713-(Bromomethyl)-4-nitrobenzoic acid

Product 1

HCID 89739572HCID 89739572, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-78 °C

Procedure

An aqueous solution of 25% w/v ammonia (100 mL) was treated with EtOH (200 mL) and cooled to −78° C. The mixture was slowly treated with a cooled (−78° C.) solution of the benzylbromide (2.58 g, 10.0 mmol) in ethanol (100 mL). The mixture was then allowed to come to room temperature and stirred for 48 h. The mixtures were evaporated under reduced pressure and the residue solid was washed with CH2Cl2 to afford 3-(aminomethyl)-4-nitrobenzoic acid (1.7 g, 87% yield).

Workup

  1. additionThe mixture was slowly treated with
  2. customto come to room temperature
  3. customThe mixtures were evaporated under reduced pressure
  4. washthe residue solid was washed with CH2Cl2

Sources & evidence

ORD record
ord-2c799aa0333a4e54a15f7bc6b8881051
Source dataset
uspto-grants-2016_03
Patent number
US09284299B2

Reaction notes

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