3-Chlorotoluene → HCID 70553526, compound

HRID 1156705Notes

Reaction equation

HRID 1156705 reaction equation
Cl.[C:2]([NH:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:17])[CH:11]=1)=[O:9])([CH3:5])([CH3:4])[CH3:3].C[O-].[Na+].[C:21]1([CH3:28])[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1>CN(C)C=O>[ClH:27].[C:2]([NH:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:23]2[CH:22]=[C:21]([CH3:28])[CH:26]=[CH:25][CH:24]=2)=[C:12]([OH:17])[CH:11]=1)=[O:9])([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 79313-ChlorotolueneHCID 30157041-(3,4-Dihydroxyphenyl)-2-((1,1-dimethylethyl)amino)ethan-1-one hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 70553526HCID 70553526, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using a procedure similar to that described above in Example 58A, 13 g. of 3,4-dihydroxyphenyl tert-butylaminomethyl ketone hydrochloride was reacted with 8 g. of sodium methoxide in 200 ml. of N,N-dimethylformamide under an atmosphere of nitrogen and then 8 g. of m-toluyl chloride was added to produce 3-hydroxy-4-(m-toluyloxy)phenyl tert-butylaminomethyl ketone hydrochloride. This salt was converted to the free base which was treated with acetic acid to yield 11.5 g. of the acetate salt, m.p. 170°-175° C. By treating a slurry of this salt in 100 ml of N,N-dimethylformamide with 40 g. of methanesulfonic acid there was obtained 10.6 g. of the corresponding methanesulfonate salt, m.p. >250° C. (uncorr.). This methanesulfonate (10 g.) was catalytically hydrogenated, using a procedure similar to that described above in Example 30B, to yield 5.4 g. of 3-hydroxy-4-(m-toluyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol methanesulfonate as a white crystalline solid which melted at 165°-168° C. (uncorr.).

Sources & evidence

ORD record
ord-00914568456743cfa6d0a8ffb3bb11b5
Source dataset
uspto-grants-1982_06
Patent number
US04336400

Reaction notes

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