Methylamine → 1-(5-Chloro-6-methoxynaphthalen-2-yl)ethan-1-one

HRID 1903181Notes

Reaction equation

HRID 1903181 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:16][CH3:17])=[C:7]2[N:14]=[O:15].C[O:19][C:20]1C=CC(C=O)=C[CH:21]=1.CN.[Cl:30][C:31]1[C:40]([O:41][CH3:42])=[CH:39][CH:38]=[C:37]2[C:32]=1[CH:33]=[CH:34][C:35](O)=[C:36]2N=O.ClC1C(OC)=CC=C2C=1C=CC(O)=C2>C(O)C>[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:16][CH3:17])=[C:7]2[N:14]=[O:15].[Cl:30][C:31]1[C:40]([O:41][CH3:42])=[CH:39][CH:38]=[C:37]2[C:32]=1[CH:33]=[CH:34][C:35]([C:20](=[O:19])[CH3:21])=[CH:36]2

Participants

8

Reactant 5

HCID 6329MethylamineHCID 312444-MethoxybenzaldehydeHCID 20468299HCID 20468299, compoundHCID 20468307HCID 20468307, compoundHCID 20468310HCID 20468310, compound

Product 2

HCID 158904591-(5-Chloro-6-methoxynaphthalen-2-yl)ethan-1-oneHCID 20468310HCID 20468310, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of the title is prepared by following essentially the same procedure described in example 2 but starting from 5-chloro-6-methoxy-2-methylamino-1-nitrosonaphthalene instead of 2-methylamino-1-nitrosonaphthalene and employing 4-methoxybenzaldehyde instead of 4-ethoxybenzaldehyde. Yield 48%. M.p. 247°-48° C. (from ethanol). The starting 5-chloro-6-methoxy-2-methylamino-1-nitrosonaphthalene is prepared through reaction of methylamine with 5-chloro-6-methoxy-1-nitroso-2-naphthol following the procedure described in the second portion of the foregoing example. In its turn this last compound is prepared by nitrosation of 5-chloro-6-methoxy-2-naphthol obtained from (5-chloro-6-methoxy-2-naphthalenyl)-ethanone which is a commercial product.

Workup

  1. customThe compound of the title is prepared

Sources & evidence

ORD record
ord-548821ebabd042ae8b9070129c1db1a7
Source dataset
uspto-grants-1984_03
Patent number
US04435417

Reaction notes

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