2-Nitroaniline → HCID 60207712, compound

HRID 1776133Notes

Reaction equation

HRID 1776133 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18]>N1C=CC=CC=1>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2])=[O:18]

Participants

4

Reactant 2

HCID 69462-NitroanilineHCID 898486-Bromohexanoyl chloride

Product 1

HCID 60207712HCID 60207712, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-nitroaniline (13.82 g, 100 mmol) in pyridine (120 mL) at 0° C. was dropwise added 6-bromohexanoyl chloride (22.6 mL, 32 g, 150 mmol) over 15 minutes. The resulting mixture was stirred for 1.5 hours at the same temperature, then poured into ice-water (500 mL) and extracted with ethyl acetate (2×200 mL). The combined organic phase was washed with aqueous citric acid solution (2×100 mL), water (100 mL) and brine (50 mL). After removal of the solvent, the crude product was passed through a silica gel pad (100 g) and washed with 1:1 mixture of hexane and diethyl ether. Concentration of the appropriate fractions gave 28.4 g of 2 as yellow solid. LC-MS (M++1) 315

Workup

  1. customat 0° C.
  2. customover 15 minutes
  3. extractionextracted with ethyl acetate (2×200 mL)
  4. washThe combined organic phase was washed with aqueous citric acid solution (2×100 mL), water (100 mL) and brine (50 mL)
  5. customAfter removal of the solvent
  6. washwashed with 1:1 mixture of hexane and diethyl ether

Sources & evidence

ORD record
ord-4a2bef2794924c93953d546784706eb4
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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