Potassium Hydroxide → 2-Nitro-4-fluoro-5-(pyrrolidin-1-yl)aniline

HRID 1004583Notes

Reaction equation

HRID 1004583 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7](Cl)=[CH:6][C:5]=1[NH:12]C(=O)C)([O-:3])=[O:2].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.[OH-].[K+].[K+].[Br-]>CS(C)=O>[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:6][C:5]=1[NH2:12])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 31268PyrrolidineHCID 253877Potassium BromideHCID 2773811N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide

Product 1

HCID 29587482-Nitro-4-fluoro-5-(pyrrolidin-1-yl)anilineYield 85.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Nitro-4-fluoro-5-(pyrrolidin-1-yl)aniline (12.3 g, 85%) was prepared by an analogous procedure to that described in preparation 1 (step 3) using N-(2-nitro-4-fluoro-5-chlorophenyl)acetamide (15.0 g, 0.064 mol) (obtained in preparation 1, step 2), pyrrolidine (22.9 g, 0.32 mol), potassium hydroxide (5.4 g, 0.096 mol) and dimethyl sulfoxide (60 mL). mp 115-116° C.; IR (KBr) 3478, 1536 cm-1 ; 1H NMR (CDCl3) δd 1.98 (m, 4H, (CH2)2), 3.50 (m, 4H, N(CH2)2), 5.64 (d, J=7.8 Hz, 1H), 6.09 (brs, 2H, NH2), 7.72 (d, J=14.6 Hz, 1H); Mass (m/z) 225 (M+.).

Workup

  1. customthat described in preparation 1 (step 3)

Sources & evidence

ORD record
ord-25d6d255bf3d424986e10acb2fbf5f3d
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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