Dichloromethane → HCID 22397142, compound

HRID 411225Notes

Reaction equation

HRID 411225 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:19])[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]2=[O:18].BrN1C(=O)CCC1=O.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C(Cl)Cl>ClC(Cl)C.CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([CH2:19][N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7]2=[O:18]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 67184N-bromobutanimideHCID 22397150HCID 22397150, compound

Product 1

HCID 22397142HCID 22397142, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Ethyl 8-chloro-1,6-dimethyl-4-oxo-1,4-dihydro[1,7]naphthyridine-3-carboxylate (Preparation 44, 0.62 g) and N-bromosuccinimide (0.45 g) are dissolved in dichloro-ethane (100 mL). The solution is subjected to light by shining a 650 W sunlamp with stirring for 25 minutes. Solvent is evaporated and the crude solid obtained is dissolved in DMF (15 mL). Morpholine (0.86 g) is added and the mixture stirred for 18 hours. The mixture is poured into CH2Cl2 (200 mL) and then washed with water (3×200 mL). The organics are dried with Na2SO4, filtered and the solvent evaporated. The crude solid is chromatographed with MeOH/CH2Cl2 (0-5%) to obtain 0.32 g (40%) of the title compound as a light orange solid. Physical characteristics: MS (ESI+) m/z 366 (M+H).

Workup

  1. customSolvent is evaporated
  2. customthe crude solid obtained
  3. stirringthe mixture stirred for 18 hours
  4. washwashed with water (3×200 mL)
  5. dry with materialThe organics are dried with Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe crude solid is chromatographed with MeOH/CH2Cl2 (0-5%)

Sources & evidence

ORD record
ord-826c0299100146a3b8e10c4c2a391911
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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