Acetyl chloride → 8-Bromo-[1,6]naphthyridin-2-ylamine dihydrochloride

HRID 1180572Notes

Reaction equation

HRID 1180572 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([Br:18])[CH:12]=[N:13][CH:14]=2)[N:9]=1)(C)(C)C.C([Cl:23])(=O)C.CCOC(C)=O>CO>[ClH:23].[ClH:23].[Br:18][C:11]1[CH:12]=[N:13][CH:14]=[C:15]2[C:10]=1[N:9]=[C:8]([NH2:7])[CH:17]=[CH:16]2

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 58979577(8-Bromo-[1,6]naphthyridin-2-yl)-carbamic acid tert-butyl ester

Product 1

HCID 691019218-Bromo-[1,6]naphthyridin-2-ylamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(8-Bromo-[1,6]naphthyridin-2-yl)-carbamic acid tert-butyl ester (1 equiv.) is suspended in methanol (10 mL). Acetyl chloride (ca. 1 mL) is added over 1 minute. After the reaction mixture cools to ambient temperature, the solvent is brought briefly to reflux using a heat gun. The heat gun is applied twice more, at which point TLC (1:1 EtOAc:hexanes) indicated complete reaction. Concentration, followed by trituration twice with dry methanol affords the title compound as a white solid, LC/MS (M+H) 224.1.

Workup

  1. customcools to ambient temperature
  2. temperatureto reflux
  3. customreaction
  4. concentrationConcentration

Sources & evidence

ORD record
ord-8f30668e12544aafb370b778ee674ffa
Source dataset
uspto-grants-2007_10
Patent number
US07282506B2

Reaction notes

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