4-Methylmorpholine → 2-Amino-5-nitrobenzamide

HRID 591862

Reaction equation

HRID 591862 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.C([N:17]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[OH-].[NH4+]>C1COCC1>[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:17])=[O:5]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 120322-Amino-5-nitrobenzoic acidHCID 14923Ammonium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 976652-Amino-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-amino-5-nitro-benzoic acid (12.9 g, 81.9 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCl) (17.3 g, 90.1 mmol), 1-hydroxybenzotriazole hydrate (HOBt) (12.2 g, 90.1 mmol) in THF (200 mL) was added 4-methylmorpholine (NMM) (9.91 mL, 90.1 mmol). After 10 minutes, ammonium hydroxide (50% v/v, 50 mL) was added. The mixture was stirred at room temperature under nitrogen for 17 hours. Solvent was removed under reduced pressure. Water was added. The solid separated was filtered, washed with aqueous NaHCO3 solution, and with water, and dried in air, to afford 2-amino-5-nitro-benzamide as a yellow solid. Yield: 9.88 g (66%).

Workup

  1. customSolvent was removed under reduced pressure
  2. additionWater was added
  3. customThe solid separated
  4. filtrationwas filtered
  5. washwashed with aqueous NaHCO3 solution
  6. dry with materialwith water, and dried in air

Sources & evidence

ORD record
ord-72088be0d9ba48f893e3b4b9895d13f0
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Linked notes

Loading…