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

HRID 1686997Notes

Reaction equation

HRID 1686997 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-7f62ddc8f8904c9580877bb29ea060c1
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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