4-(Hydroxymethyl)benzoic acid → HCID 58525758, compound

HRID 885712Notes

Reaction equation

HRID 885712 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:18][NH2:19]>ClCCl>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:19][O:18][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[O:9])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 763604-(Hydroxymethyl)benzoic acidHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamine

Product 1

HCID 58525758HCID 58525758, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(Hydroxymethyl)benzoic acid (0.75 g, 5 mmol), O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (0.59 g, 5 mmol), and 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (1.15 g, 6 mmol) in dichloromethane (50 mL) was stirred at room temperature for 2 h (monitored by TLC). The mixture was extracted with water and dried over magnesium sulfate. The residue was purified by chromatography (MeOH:DCM=1:50) to give the title compound (0.88 g, 70%). NMR (400 MHz in DMSO, Bruker AVANCE-400): δ 1.52 (m, 3H, OTHP), 1.72 (m, 3H, OTHP), 3.51 (m, 1H, OTHP), 4.04 (m, 1H, OTHP), 4.53 (s, 2H, CH2), 4.98 (s, 1H, OTHP), 5.28 (s, 1H, NH), 7.38 (d, 2H, J=10.0 Hz, Ar—H), 7.72 (d, 2H, J=5.0 Hz, Ar—H), 11.55 (s, 1H, OH).

Workup

  1. extractionThe mixture was extracted with water
  2. dry with materialdried over magnesium sulfate
  3. customThe residue was purified by chromatography (MeOH:DCM=1:50)

Sources & evidence

ORD record
ord-5dc3e59029ba4ebe8affbfd5b116d732
Source dataset
uspto-grants-2012_08
Patent number
US08242282B2

Reaction notes

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