Sodium Carbonate → HCID 22877459, compound

HRID 1379877Notes

Reaction equation

HRID 1379877 reaction equation
[NH2:1][C@@H:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].[N+:14]([O-])([O-:16])=[O:15].[K+].C(=O)([O-])[O-].[Na+].[Na+]>S(=O)(=O)(O)O>[NH2:1][C@@H:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 10103689(R)-3-amino-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

Product 1

HCID 22877459HCID 22877459, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 440 mg (2.50 mmol) of 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Example 1, Step E) in 5 mL of concentrated sulfuric acid at 0° C. was added 265 mg (2.63 mmol) of potassium nitrate. The resulting yellow solution was stirred for 30 minutes at then at room temperature for 24 hours. The reaction mixture was poured carefully into 100 g of ice and the pH of the resulting mixture was adjusted to 11 by the portionwise addition of sodium carbonate. The mixture was transferred to a separatory funnel and extracted thoroughly with ethyl acetate (4×100 mL). The organic extracts were combined, washed with brine (100 mL), dried over sodium sulfate and filtered. The solvent was removed under vacuum to afford 385 mg (70%) of the product as a yellow solid. 1H NMR (200 MHz, CDCl3): δ 1.58 (s, 2H), 1.98 (m, 1H), 2.47-2.70 (m, 1H), 2.72-3.05 (m, 2H), 3.40 (dd; 11, 8 Hz; 1H), 7.07 (d, 8 Hz, 1H), 7.92 (s, 1H), and 8.10 (m, 1H). FAB-MS: calculated for C10H11N3O3 221; found 222 (M+H,100%).

Workup

  1. customThe mixture was transferred to a separatory funnel
  2. extractionextracted thoroughly with ethyl acetate (4×100 mL)
  3. washwashed with brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-b043600b7c4146e9bd3bd9c88f89d3a6
Source dataset
uspto-grants-1997_09
Patent number
US05672596

Reaction notes

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