4-Hydroxybenzoic Acid → 4-Hydroxybenzamide

HRID 1841875Notes

Reaction equation

HRID 1841875 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[N:18]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:18])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 650524-Hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of freshly prepared 4-hydroxybenzoic acid (635 mg; 4.6 mmol) and BOP (1.7 g; 5.06 mmol) in DMF (20 mL) was added dropwise and at room temperature to a solution of PEI (1 g, 23.2 mmol) in DMF (50 mL). After 2 hours under stirring, the DMF was removed by evaporation under reduced pressure. The crude product was taken in water, dissolved by addition of aqueous sodium hydroxide solution 1M (pH 11) and subjected to dialysis using a SpectraPor 12-14 kDa membrane against water (1 L, 2 changes over 24 h). Lyophilization provided 4-hydroxybenzamide-PEI (0.7 g) at a modification degree of 28%. 1H NMR (D2O) δppm: 2.6 (bm, 2.9H, —NHCH2CH2NH—), 3.22 (m, 0.55H, Phe-CONHCH2CH2NH—), 3.35 (m, 0.55H, Phe-CONHCH2CH2NH) 6.57 (d, J=7.3 Hz, 0.55 H, CHaro), 6.97 (m, 0.55H, CHaro).

Workup

  1. customthe DMF was removed by evaporation under reduced pressure
  2. dissolutiondissolved by addition of aqueous sodium hydroxide solution 1M (pH 11)
  3. customsubjected to dialysis
  4. customagainst water (1 L, 2 changes over 24 h)

Sources & evidence

ORD record
ord-1123e1cfa31346568212ddbfce7260de
Source dataset
uspto-grants-2015_02
Patent number
US08945927B2

Reaction notes

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