Hydrochloric Acid → HCID 10359141, compound

HRID 720416Notes

Reaction equation

HRID 720416 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].[BH4-].[Na+].Cl>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:16]([OH:25])[C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 11723894HCID 11723894, compound

Product 1

HCID 10359141HCID 10359141, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-cyano-(4-methoxy-benzoyl)-pyrrolo[1,2-a]quinoline (5.2 mg, 0.0159 mmol) in 5 mL of methanol at room temperature was added sodium borohydride (5.3 mg, 0.14 mmol) and it was stirred overnight at room temperature. Upon the completion of the reaction, 2 drops of aqueous 1N HCl was added and the reaction mixture was evaporated to near dryness. The residue was dissolved in 15 mL of ethyl acetate, washed with water, saturated NaCl and the organic layer was dried over anhydrous Na2SO4, filtered and evaporated. The crude was purified by chromatography (30% ethyl acetate/hexane) to yield the title compound (5.1 mg, 97%). 1H NMR (CDCl3): 8.69 (d, J=8.40 Hz, 1H), 7.77 (dd, J=7.80, 1.80 Hz, 1H), 7.57 (m, 2H), 7.47 (m, 1H), 7.38 (m, 3H), 6.95 (dt, J=8.42, 2.12 Hz, 2H), 6.59 (s, 1H), 6.51 (d, J=4.2 Hz, 1H), 3.84 (s, 3H), 2.64 (d, J=4.8, 1H).

Workup

  1. additionwas added
  2. customthe reaction mixture was evaporated
  3. dissolutionThe residue was dissolved in 15 mL of ethyl acetate
  4. washwashed with water, saturated NaCl
  5. dry with materialthe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude was purified by chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c3970cf5e7dd4d75b39910276dd024a2
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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