Hydrochloric Acid → HCID 69020040, compound

HRID 1375281Notes

Reaction equation

HRID 1375281 reaction equation
[NH2:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].Cl.[OH-].[Na+].[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:20][C:21](Cl)=[O:22])=[CH:15][CH:14]=1>O>[CH2:19]([O:20][C:21](=[O:22])[NH:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9])[C:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 4328274-Aminoresorcinol

Product 1

HCID 69020040HCID 69020040, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a cooled solution (0° C.) of 4-amino resorcinol.HCl (1.0 g, 6.18 mmol) in H2O (10 mL) was added dropwise aq. NaOH (0.49 g, 12.3 mmol) in H2O (15 mL). To this mixture were added slowly Cbz-Cl (Carbobenzoxy chloride, 1.06 mL, 7.43 mmol) and NaOH (0.25 g) in H2O (5 mL). After stirring for 1 h at room temperature, the mixture was extracted with EtOAc (2×50 mL). The organic layer was dried over MgSO4 (10 g), filtrated and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc:hexane=1:5) to give (2,4-dihydroxyphenyl)-carbamic acid benzyl ester (KCBG02. 1.28 g, 80%).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×50 mL)
  2. dry with materialThe organic layer was dried over MgSO4 (10 g)
  3. filtrationfiltrated
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel (EtOAc:hexane=1:5)

Sources & evidence

ORD record
ord-1a08fcfca39c4a0b9621d6b6c3bb20ae
Source dataset
uspto-grants-2007_01
Patent number
US07166744B2

Reaction notes

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