4-Hydroxybenzoic Acid → 4-Hydroxybenzamide

HRID 1841874Notes

Reaction equation

HRID 1841874 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 (476 mg; 3.45 mmol) and BOP (1.7 g; 3.8 mmol) in DMF (20 mL) was added dropwise and at room temperature to a solution of PEI (1 g, 23.2 mmol) in DMF (30 mL). After 2 hours under stirring, the DMF was removed by evaporation under vacuum. The residue was taken in water (25 mL), dissolved by addition of aqueous sodium hydroxide solution 1M (pH 10) and subjected to dialysis using a SpectraPor 12-14 kDa membrane against water hydrochloric acid 50 mM (1 L volume; 2 changes over 24 h) and water (1 L). Lyophilization provided 4-hydroxybenzamide-PEI (1 g) at a modification degree of 13%. 1HNMR (D2O) δppm: 3.8-2.45 (m, 4H, NHCH2CH2NH), 6.9 (m, 0.25H, CHaro), 7.18 (m, 0.25H, CHaro).

Workup

  1. customthe DMF was removed by evaporation under vacuum
  2. dissolutiondissolved by addition of aqueous sodium hydroxide solution 1M (pH 10)
  3. customsubjected to dialysis
  4. customagainst water hydrochloric acid 50 mM (1 L volume; 2 changes over 24 h) and water (1 L)

Sources & evidence

ORD record
ord-fe1333c5e7414c1995d313ebd0cf237a
Source dataset
uspto-grants-2015_02
Patent number
US08945927B2

Reaction notes

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