Hydrochloric Acid → 5-Amino-2,3-dichlorophenol hydrochloride

HRID 38554Notes

Reaction equation

HRID 38554 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([OH:14])[C:11]([Cl:15])=[C:10]([Cl:16])[CH:9]=1)(C)(C)C.Cl.O1CCOCC1>CC(O)C>[ClH:15].[NH2:7][C:8]1[CH:9]=[C:10]([Cl:16])[C:11]([Cl:15])=[C:12]([OH:14])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58116863HCID 58116863, compound

Product 1

HCID 668498095-Amino-2,3-dichlorophenol hydrochlorideYield 189.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl(3,4-dichloro-5-hydroxyphenyl)carbamate from Example 67A (960 mg, 3.45 mmol) was dissolved in 2-propanol (16 mL), and 4 M gaseous hydrogen chloride in dioxane (5.0 mL, 20 mmol) was added. The mixture was heated to 80° C. for 1.5 h. Subsequently, the solvent was removed in vacuo to yield 700 mg (90%) of the title compound.

Workup

  1. customSubsequently, the solvent was removed in vacuo

Sources & evidence

ORD record
ord-d5c8457c6c0a455d8ac0c921a5f02529
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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