2-Amino-5-chloropyridine → 3-amino-N-(5-chloropyridin-2-yl)-2-naphthamide

HRID 2223369Notes

Reaction equation

HRID 2223369 reaction equation
[NH:1]1[C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][C:5]=2[C:4](=[O:15])OC1=O)[CH:12]=[CH:11][CH:10]=[CH:9]3.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1>C1(C)C(C)=CC=CC=1.CN(C)C1C=CN=CC=1>[NH2:1][C:6]1[C:5]([C:4]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=2)=[O:15])=[CH:14][C:13]2[C:8]([CH:7]=1)=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

5

Reactant 2

HCID 661742-Amino-5-chloropyridineHCID 2944812H-naphtho[2,3-d][1,3]oxazine-2,4(1H)-dione

Product 1

HCID 231250193-amino-N-(5-chloropyridin-2-yl)-2-naphthamideYield 8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 2H-naphth[2,3-d][1,3]oxazine-2,4(1H)-dione (216 mg) and 2-amino-5-chloropyridine (202 mg) in xylene (5 ml) is stirred at 150° C. for 13 hours, and thereto added 4-dimethylaminopyridine (14.4 mg) and the mixture is stirred at 150° C. for another 3 hours. The reaction solution is concentrated under reduced pressure and the resulting residue is suspended in ethyl acetate, and filtered to remove insoluble materials. The filtrate is concentrated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give 3-amino-N-(5-chloropyridin-2-yl)-2-naphthamide (24 mg).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. filtrationfiltered
  3. customto remove insoluble materials
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-c6251bdbe98a4de28a691d45717f2dc2
Source dataset
uspto-grants-2008_05
Patent number
US07375119B2

Reaction notes

Loading…