Nabumetone → 6-Methoxy-2-naphthaldehyde

HRID 1954497Notes

Reaction equation

HRID 1954497 reaction equation
BrC1C=C2C(=CC=1)C=C([OH:12])C=C2.CC(C[CH2:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:22]=[C:23]([O:28][CH3:29])[CH:24]=[CH:25][C:26]=2[CH:27]=1)=O.BrC1C=C2C(=CC=1)C=C(OC)C=C2>CN(C)C=O>[CH3:29][O:28][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[CH:27]=[C:18]([CH:17]=[O:12])[CH:19]=[CH:20]2

Participants

5

Reactant 3

HCID 4409Nabumetone2×HCID 271446-Bromo-2-naphthalenol2×HCID 787862-Bromo-6-methoxynaphthalene2×

Product 1

HCID 769916-Methoxy-2-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

When it is wished to convert the 6-bromo-2-naphthol to nabumetone, the 6-bromo-2-naphthol is first converted to a 6-bromo-2-methoxynaphthalene intermediate as described above, and the intermediate is then converted to nabumetone by any of the techniques already known for that conversion. For example, as described in U.S. Pat. No. 5,225,603 (Aslam et al.), the 6-bromo-2-methoxynaphthalene may be (a) reacted with N,N-dimethylformamide to form 6-methoxy-2-naphthaldehyde, which is then condensed with acetone to prepare a 4-(6-methoxy-2-naphthyl)-3-buten-2-one intermediate that is then catalytically hydrogenated to nabumetone or (b) reacted with methyl vinyl ketone to form the 4-(6-methoxy-2-naphthyl)-3-buten-2-one intermediate that is then catalytically hydrogenated to nabumetone.

Sources & evidence

ORD record
ord-ffd10bee2f4b412ab13f85c2f39dadfa
Source dataset
uspto-grants-2000_09
Patent number
US06121500

Reaction notes

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