HCID 86052444, compound → HCID 68931152, compound

HRID 521269Notes

Reaction equation

HRID 521269 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[O:21])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[OH:21])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 86052444HCID 86052444, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 68931152HCID 68931152, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the general method described in Step 7 of Example 1, 6-(3-nitroquinolin-4-ylamino)hexanal (9.9 g, 34.5 mmol) was reacted with phenylmagnesium bromide (36.2 mL of a 1 M solution in THF, 36.2 mmol) to provide 6-(3-nitroquinolin-4-ylamino)-1-phenylhexan-1-ol (4.4 g) as a bright yellow solid after chromatography on silica gel (elution with ethyl acetate and hexane, 1:1, volume:volume).

Sources & evidence

ORD record
ord-e946df82b7fc4fb2a396982541c0a97f
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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