Nitric Acid → (5-Chloro-2-nitrophenyl)acetamide

HRID 1004585Notes

Reaction equation

HRID 1004585 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH2:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[N+:12]([O-])([OH:14])=[O:13].OS(O)(=O)=O.[K+].[Br-]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[C:4]([CH2:8][C:9]([NH2:11])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 253877Potassium BromideHCID 53247462-(3-Chlorophenyl)acetamide

Product 1

HCID 18792738(5-Chloro-2-nitrophenyl)acetamideYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5-Chloro-2-nitrophenyl)acetamide (35.0 g, 30%) was prepared from 3-chloro phenyl acetamide (90.0 g, 0.53 mol) (obtained in step 1 above), conc. HNO3 (100 mL), conc. H2SO4 (156 mL) and dichloromethane (250 mL), by an analogous procedure to that described in preparation 1 (step 2). mp 115-116° C.; IR (KBr) 3329, 1693, 1504 cm-1 ; 1H NMR (CDCl3) δ 2.30 (s, 3H, CH3), 7.12 (d, J=8.4 Hz, 1H), 7.28 (s, 1H), 8.20 (d, J=8.4 Hz, 1H), 10.48 (brs, 1H, NH); Mass (m/z) 214 (M+.).

Workup

  1. customthat described in preparation 1 (step 2)

Sources & evidence

ORD record
ord-8b9f65eb45134512ae11f44002f68460
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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