Dimethylamine → 2-Naphthol, 6-bromo-1-methyl-

HRID 1359189Notes

Reaction equation

HRID 1359189 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[C:7]([OH:13])[CH:6]=[CH:5]2.Br[C:15]1C=C2C(=CC=1)C=C(O)C=C2.CNC.C=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:15])=[C:7]([OH:13])[CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 271446-Bromo-2-naphthalenol2×HCID 220481596-Bromo-1-chloronaphthalen-2-ol

Product 1

HCID 279772-Naphthol, 6-bromo-1-methyl-

Procedure

Preparation of 6-bromo-1-chloro-2-naphthol 4 from the corresponding 6-bromo-2-naphthol 3 is described in the literature (Buu-Hoi, JOC 1951, 16, 185), Scheme II. 6-Bromo-1-methyl-2-naphthol 7 was prepared as depicted in reaction Scheme II. Reaction of 6-bromo-2-naphthol 3 with aqueous dimethyl amine and aqueous formaldehyde in alcohol afforded the Mannich product 5. Reaction of 5 with acetyl chloride in methylene chloride or chloroform afforded the acetate 6. Hydride reduction of 6 in a solvent such as ethanol followed by basic work-up yielded the desired 6-bromo-1-methyl-2-naphthol 7.

Workup

  1. customas depicted in reaction Scheme II

Sources & evidence

ORD record
ord-92c5e4bd17bb4eebb98e4fe4a06b8f0b
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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