Sodium Hydroxide → HCID 18510482, compound

HRID 1370185Notes

Reaction equation

HRID 1370185 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]1[C:10]2=[CH:11][C:12]3[CH:13]=[CH:14][CH:15]=[N:16][C:17]=3[N:9]2[CH2:8][CH2:7]1.[OH-].[Na+].CC1C=CC([CH2:27][O:28]C(NNC(C2C=NC=CN=2)=O)=O)=CC=1>CN(C)C=O>[CH2:6]1[C:10]2=[C:11]([CH:27]=[O:28])[C:12]3[CH:13]=[CH:14][CH:15]=[N:16][C:17]=3[N:9]2[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 18510478HCID 18510478, compound

Product 1

HCID 18510482HCID 18510482, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

Phosphorus oxychloride (3.85 ml) was added dropwise to N,N-dimethylformamide (25 ml) cooled in an ice-bath. The mixture was stirred 10 min before the addition of 2,3-dihydro-1H-3a,4-diaza-cyclopenta[a]indene (4.40 g) in N,N-dimethylformamide (7 ml). The mixture was stirred 45 min at 40° C., cooled to room temperature and concentrated aqueous sodium hydroxide added dropwise to pH10. The mixture was heated at 50° C. 10 min, cooled to room temperature and poured onto crushed ice. The organics were extracted with ethyl acetate (2×), the combined organic phases washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane 1:1 to 1:0) to afford 2,3-dihydro-1H-3a,4-diaza-cyclopenta[a]indene-8-carbaldehyde (2.4 g, 46%) as a light orange oil which solidified on standing. Mp. 137-141; MS (EI): 187 (M+H)+, 143, 100; 1H NMR (δ, CDCl3) 10.01 (s, 1H), 8.45 (dd, 1H, J=1,8 Hz), 8.32 (dd, 1H, J=1,5 Hz), 7.23 (dd, 1H, J=5,8 Hz), 4.31 (t, 2H, J=6 Hz), 3.38 (t, 2H, J=8 Hz), 2.76 (dt, 2H, J=6,8 Hz) ppm.

Workup

  1. temperaturecooled in an ice-bath
  2. temperaturecooled to room temperature
  3. temperatureThe mixture was heated at 50° C
  4. temperature10 min, cooled to room temperature
  5. additionpoured
  6. customonto crushed ice
  7. extractionThe organics were extracted with ethyl acetate (2×)
  8. washthe combined organic phases washed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel (ethyl acetate/hexane 1:1 to 1:0)

Sources & evidence

ORD record
ord-6c7621405f7b4ca182a7c6a8dc317b6e
Source dataset
uspto-grants-2003_06
Patent number
US06583134B2

Reaction notes

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