5,6,7,8-Tetrahydro-1-nitro-2-naphthalenol → Methyl 5-bromo-2(5,6,7,8-tetrahydro-1-nitro-2-naphthyloxy)valerate

HRID 414065Notes

Reaction equation

HRID 414065 reaction equation
[N+:1]([C:4]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][C:5]=1[OH:14])([O-:3])=[O:2].Br[CH:16]([CH2:21][CH2:22][CH2:23][Br:24])[C:17]([O:19][CH3:20])=[O:18]>>[Br:24][CH2:23][CH2:22][CH2:21][CH:16]([O:14][C:5]1[CH:6]=[CH:7][C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[C:4]=1[N+:1]([O-:3])=[O:2])[C:17]([O:19][CH3:20])=[O:18]

Participants

3

Reactant 2

HCID 49137365,6,7,8-Tetrahydro-1-nitro-2-naphthalenolHCID 10912698Methyl 2,5-dibromopentanoate

Product 1

HCID 21282569Methyl 5-bromo-2(5,6,7,8-tetrahydro-1-nitro-2-naphthyloxy)valerate

Procedure

In a manner similar to that of Reference Example 5, 5,6,7,8-tetrahydro-1-nitro-2-naphthol was allowed to react with methyl 2,5-dibromovalerate to give methyl 5-bromo-2(5,6,7,8-tetrahydro-1-nitro-2-naphthyloxy)valerate, which was then allowed to react, in a manner similar to that of Reference Example 8, with 1-(4-fluorophenyl)piperazine to obtain methyl 5-[4-(4-fluorophenyl)-1-piperazinyl]-2-(5,6,7,8-tetrahydro-1-nitro-2-naphthyloxy)valerate as an oily product. The overall yield was 65.1%. NMR(CDCl3)δ: 1.55-2.17(8H,m), 2,41(2H,5,J=7.2 Hz), 2.52-2.81(8H,m), 2.96-3.14(4H,m), 3.72(3H,s), 4.67(1H,t,J=6 Hz), 6.55-7.11 (6H,m)

Sources & evidence

ORD record
ord-7a938f8e02904124ac96e19c8ecf0f87
Source dataset
uspto-grants-1988_12
Patent number
US04789675

Reaction notes

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