Pyridine → HCID 10195526, compound

HRID 1007140Notes

Reaction equation

HRID 1007140 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:11]([CH2:13][C:14]([O:16]C)=[O:15])[CH2:10][NH:9][C:8]=2[CH:18]=1)([O-])=O.[C:19](=[O:22])([O-])[O-].[Na+].[Na+].[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CN(C=O)C.C(OCC)(=O)C>[C:25]([N:9]1[C:8]2[CH:18]=[C:4]([NH:1][C:19](=[O:22])[CH2:8][CH2:18][CH2:4][NH:1][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=3)[CH:5]=[CH:6][C:7]=2[O:12][CH:11]([CH2:13][C:14]([OH:16])=[O:15])[CH2:10]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 60110357HCID 60110357, compound

Product 1

HCID 10195526HCID 10195526, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of methyl (6-nitro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)acetate 2 (2.52 g, 10 mmol) and anhydrous sodium carbonate (2 g.) in anhydrous DMF (15 mL) and anhydrous pyridine (5 mL), benzoyl chloride (1.5 mL, 12.96 mmol) was added. The resulting suspension was stirred 8 hours at room temperature. The reaction mixture was then diluted with ethyl acetate (100 mL) and washed with water (3×100 mL). After separation the organic phase was dried (Na2SO4) and evaporated to dryness in vacuo to afford the title compound (3.3 g, 93%) as a yellow-orange oil.

Workup

  1. additionwas added
  2. washwashed with water (3×100 mL)
  3. customAfter separation the organic phase
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-f2455d767ac2432ea52c77ea9eba08d1
Source dataset
uspto-grants-2004_09
Patent number
US06794385B2

Reaction notes

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