Sodium Carbonate → HCID 66666248, compound

HRID 406173Notes

Reaction equation

HRID 406173 reaction equation
O=P(Cl)(Cl)[Cl:3].[C:6]1([C:12]2[CH:13]=[C:14]3[C:19](=[N:20][C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N+:18]([O-])=[CH:17][CH:16]=[CH:15]3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:29]1([C:35]2[C:44]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[CH:43][C:42]3[C:37](=[N:38][CH:39]=[CH:40][CH:41]=3)[N+:36]=2[O-])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>>[Cl:3][C:17]1[N:18]=[C:19]2[C:14]([CH:13]=[C:12]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:20]2)=[CH:15][CH:16]=1.[Cl:3][C:41]1[CH:40]=[CH:39][N:38]=[C:37]2[C:42]=1[CH:43]=[C:44]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:35]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[N:36]2

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 66666120HCID 66666120, compoundHCID 66666286HCID 66666286, compound2×

Product 2

HCID 66666248HCID 66666248, compoundHCID 86681846HCID 86681846, compound

Procedure

POCl3 (10 ml, 107 mmol) was added dropwise to a mixture of 6,7-diphenyl-1,8-naphthyridine 1-oxide and 2,3-diphenyl-1,8-naphthyridine 1-oxide (Intermediates C) (3 g, 10.06 mmol) at 0° C. The reaction mixture was allowed to warm at room temperature and heated at 100° C. for 2 h. The mixture was poured carefully onto ice/water and the pH was adjusted to pH 8-9 by addition of Na2CO3 (solid) portionwise. The aqueous layer was separated and extracted with DCM (3×150 ml). The organic portions were combined and washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford a brown oil. Purification of the crude oil by chromatography on silica eluting with 0-50% EtOAc in iso-hexane afforded 7-chloro-2,3-diphenyl-1,8-naphthyridine and 5-chloro-2,3-diphenyl-1,8-naphthyridine:

Workup

  1. temperatureheated at 100° C. for 2 h
  2. additionThe mixture was poured carefully onto ice/water
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM (3×150 ml)
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford a brown oil
  10. customPurification of the crude oil by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-66683f6d2ab0419bb71720a2f7da1dee
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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