5-[Di-(tert-butoxycarbonyl)amino]methyl-7-nitro-2,3-dimethoxyquinoxaline → 5-Aminomethyl-2,3-dimethoxy-7-nitro-quinoxaline

HRID 1953776Notes

Reaction equation

HRID 1953776 reaction equation
C(OC([N:8]([CH2:16][C:17]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[C:23]2[C:18]=1[N:19]=[C:20]([O:32][CH3:33])[C:21]([O:30][CH3:31])=[N:22]2)C(OC(C)(C)C)=O)=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][CH2:16][C:17]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[C:23]2[C:18]=1[N:19]=[C:20]([O:32][CH3:33])[C:21]([O:30][CH3:31])=[N:22]2

Participants

3

Reactant 1

HCID 232980085-[Di-(tert-butoxycarbonyl)amino]methyl-7-nitro-2,3-dimethoxyquinoxaline

Product 1

HCID 179152965-Aminomethyl-2,3-dimethoxy-7-nitro-quinoxaline

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

13.8 9 (29.7 mmol) of 5-[di-(tert-butoxycarbonyl)amino]methyl-7-nitro-2,3-dimethoxyquinoxaline are stirred at room temperature for 8 hours in 60 ml of trifluoroacetic acid. The reaction mixture is concentrated under reduced pressure and the red oil is well stirred at 0° for one hour with 1N potassium carbonate. The yellow crystals are filtered off, washed with 100 ml of water and 100 ml of a 1:1 mixture of ethyl acetate and hexane, and dried.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. filtrationThe yellow crystals are filtered off
  3. washwashed with 100 ml of water and 100 ml of a 1:1 mixture of ethyl acetate and hexane
  4. customdried

Sources & evidence

ORD record
ord-ceeffaaf095041cd815115f76703a569
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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