Hydrochloric Acid → 2-(2-Amino-ethylamino)-6-nitro-benzoic acid

HRID 1040687Notes

Reaction equation

HRID 1040687 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[C:13]=1[C:14]([OH:16])=[O:15])=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1.C(OCC)(=O)C>[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[C:13]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 672646122-(2-Tert-butoxycarbonylaminoethylamino)-6-nitro-benzoic acid

Product 1

HCID 672646922-(2-Amino-ethylamino)-6-nitro-benzoic acidYield 76%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(2-tert-butoxycarbonylamino-ethylamino)-6-nitro-benzoic acid (0.22 g, 0.00068 mol) in THF at 0° C. was added 4N HCl in dioxane (0.68 mL). The reaction was stirred at 0° C. for 2 h then warmed to room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to give 2-(2-amino-ethylamino)-6-nitro-benzoic acid (0.12, 76% yield). 1H NMR (400 MHz, CDCl3) δ 11.6 (s, 1H), 7.57 (t, 1H, J=7.6 Hz), 7.05 (d, 1H, J=7.8 Hz), 6.80 (d, 1H, J=7.8 Hz), 4.0 (broad s, 3H), 3.63 (m, 2H), 3.07 (m, 2H); MS (m/e) 226 (M+1).

Workup

  1. temperaturethen warmed to room temperature overnight
  2. washwashed with water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ff98288eacd46a6a7c333e0700daf7f
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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