Methanol → HCID 18671692, compound

HRID 1057652Notes

Reaction equation

HRID 1057652 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][C:16]#[N:17])=[CH:3][CH:2]=1.CO>C1COCC1>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:15][CH2:16][NH2:17])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 18671668(9H-Carbazol-4-yloxy)acetonitrile

Product 1

HCID 18671692HCID 18671692, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of (9H-carbazol-4-yloxy)acetonitrile (1.13 g, 5.1 mmol) in dry THF (50 mL) is added borane-methyl sulfide complex (1.4 mL, 15.3 mmol). The mixture is heated at 85° C. for 6 h. Methanol is added slowly until gas evolution ceased. The solvents are removed under reduced pressure. Methanol (20 mL) is added then removed under reduced pressure. Methanol (50 mL) and concentrated hydrochloric acid are added and the mixture heated at 65° C. overnight. The mixture is neutralized with saturated potassium carbonate and partitioned between water and CH2Cl2. The layers are separated and the organic layer washed twice with water (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography, silica gel (200 mL), using CH3OH/CH2Cl2 (4/96) gave 0.61 g (53%) of the title compound; IR (drift) 3082, 1608, 1585, 1456, 1443, 1346, 1336, 1303, 1252, 1222, 1098, 911, 782, 750, 719 cm−1. 1H NMR (DMSO-d6) δ3.05, 4.13, 6.65, 7.03, 7.12, 7.24, 7.31, 7.41, 8.12; Anal. Calcd for C14H14N2O: C, 74.31; H, 6.24; N, 12.38. Found: C, 73.90; H, 6.32; N, 12.14.

Workup

  1. additionis added borane-methyl sulfide complex (1.4 mL, 15.3 mmol)
  2. customThe solvents are removed under reduced pressure
  3. additionMethanol (20 mL) is added
  4. customthen removed under reduced pressure
  5. additionMethanol (50 mL) and concentrated hydrochloric acid are added
  6. temperaturethe mixture heated at 65° C. overnight
  7. custompartitioned between water and CH2Cl2
  8. customThe layers are separated
  9. washthe organic layer washed twice with water (100 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-e544cddd13b44ad09debe371ec8dde30
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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