Lithium Hydroxide → 3-Aminomethyl-5-nitrobenzoic acid

HRID 964490Notes

Reaction equation

HRID 964490 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([O:8]C)=[O:7].[Li+].[OH-]>C1COCC1.O>[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 19077132Methyl 3-(aminomethyl)-5-nitrobenzoate

Product 1

HCID 190771333-Aminomethyl-5-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-aminomethyl-5-nitrobenzoate (5890 mg, 28 mmol) in THF (100 mL) was added a solution of LiOH (2350 mg, 56 mmol) in water (100 mL) and the mixture was stirred at r.t. for 2.5 hours. THF was evaporated and the aqueous solution was washed with Et2O (100 mL). The solution was neutralized with concentrated HCl (6 mL) and evaporated in vacuo. To a solution of evaporated residue in water (150 mL) and concentrated HCl (3 mL) was added 1N LiOH (50 mL). Brown fine needles were precipitated out and collected on a glass filter (5300 mg, 96%): 1H NMR (300 MHz, D2O) δ 8.645 (s, 1H), 8.412 (s, 1H), 8.232 (s, 1H), 4.332 (s, 2H).

Workup

  1. customTHF was evaporated
  2. washthe aqueous solution was washed with Et2O (100 mL)
  3. customevaporated in vacuo
  4. additionTo a solution of evaporated residue in water (150 mL) and concentrated HCl (3 mL) was added 1N LiOH (50 mL)
  5. customBrown fine needles were precipitated out and
  6. customcollected on a glass
  7. filtrationfilter (5300 mg, 96%)

Sources & evidence

ORD record
ord-e8b5f9f999a64db29f7b12d1c7bc6510
Source dataset
uspto-grants-1998_06
Patent number
US05770380

Reaction notes

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