Hydrochloric Acid → 4-[2-(Phthalimido)ethyl]-2-nitrophenol

HRID 2379272Notes

Reaction equation

HRID 2379272 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])(OCC)=O.Cl.[N+:24]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=1[OH:36])[CH2:30]CN)([O-:26])=[O:25].Cl>>[C:13]1(=[O:22])[N:12]([CH2:7][CH2:30][C:29]2[CH:33]=[CH:34][C:35]([OH:36])=[C:27]([N+:24]([O-:26])=[O:25])[CH:28]=2)[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]12

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 189583293-Nitrotyramine hydrochloride

Product 1

HCID 189583334-[2-(Phthalimido)ethyl]-2-nitrophenolYield 91%

Procedure

7.58 g of potassium carbonate and 6.02 g of N-carboethoxyphthalimide were added to 180 ml of an aqueous solution of 6.01 g of 3-nitrotyramine hydrochloride and stirred for 15 hours at room temperature. 6N hydrochloric acid was gradually added to the reaction mixture at 0° C. so that the pH value of the mixture was adjusted to be 1 (one). The crystals thus precipitated out were removed by means of filtration and recrystallized from methanol to obtain 7.79 g (yield: 91%) of 4-[2-(phthalimido)ethyl]-2-nitrophenol as yellow crystals.

Workup

  1. customThe crystals thus precipitated out
  2. customwere removed by means of filtration
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-18de73ad4fa544c4adcab9f00b531bc5
Source dataset
uspto-grants-1994_11
Patent number
US05360909

Reaction notes

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