Sodium Hydroxide → HCID 69507248, compound

HRID 1768420Notes

Reaction equation

HRID 1768420 reaction equation
[C:1]([CH:3]1[C:12]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=2)=[C:11]2[C:6](=[C:7]3[CH:22]=[CH:21][N:20]=[C:8]3[CH:9]=[CH:10]2)[O:5][C:4]1=N)#[N:2].[OH-:24].[Na+]>Cl.O>[C:1]([CH:3]1[C:12]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=2)=[C:11]2[C:6](=[C:7]3[CH:22]=[CH:21][N:20]=[C:8]3[CH:9]=[CH:10]2)[O:5][C:4]1=[O:24])#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86588471HCID 86588471, compound

Product 1

HCID 69507248HCID 69507248, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3-cyano-2-imino-4-(5-methyl-pyridin-3-yl)-2H-pyrrolo[2,3-h]chromene (83 mg, 0.28 mmol) in 10% HCl (5 mL) was stirred at room temperature for approximately 5 h. The yellow suspension was diluted with water (5 mL), neutralized to approximate pH=10 using 10% NaOH and extracted with EtOAc (3×25 mL). The EtOAc extracts were washed with brine (10 mL), dried over MgSO4, and evaporated to yield a yellow solid. The solid was purified by flash column chromatography (silica gel, EtOAc:hexanes, 50-80% EtOAc) to yield a yellow solid (27 mg, 35%). 1H NMR (DMSO-d6): 12.10 (s, 1H), 8.70 (d, J=1.8 Hz, 1H), 8.58 (d, J=2.1 Hz, 1H), 7.88 (m, 1H), 7.62 (d, J=3.3 Hz, 1H), 7.45 (dd, J=0.3, 9.0 Hz, 1H), 6.91-6.88 (m, 2H), 2.45 (s, 3H).

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe EtOAc extracts were washed with brine (10 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto yield a yellow solid
  6. customThe solid was purified by flash column chromatography (silica gel, EtOAc:hexanes, 50-80% EtOAc)

Sources & evidence

ORD record
ord-b1a34f28bd7f44fba4590683d0042211
Source dataset
uspto-grants-2007_06
Patent number
US07235674B2

Reaction notes

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