Hydrochloric Acid → HCID 20197064, compound

HRID 228365Notes

Reaction equation

HRID 228365 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.[Cl-].[Cl-].[Cl-].[Al+3].[Cl:16][C:17]1[CH:18]=[C:19]([OH:28])[CH:20]=[CH:21][C:22]=1[CH:23]=[CH:24][N+:25]([O-])=O.Cl>C1COCC1.O>[NH2:25][CH2:24][CH2:23][C:22]1[CH:21]=[CH:20][C:19]([OH:28])=[CH:18][C:17]=1[Cl:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 68747527HCID 68747527, compound

Product 1

HCID 20197064HCID 20197064, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To lithium aluminum hydride 1.0 M in ether (1.50 mL, 1.50 mmol) at 0° C. a solution of aluminum trichloride (201 mg, 1.51 mmol) in THF (2 mL) is added. After 5 min a solution of compound obtained in step 1 above (100 mg, 0.50 mmol) in THF (2 mL) is added and the reaction is allowed to stir at room temperature overnight. Add water and then 3 N HCl. Extract the aqueous layer with 3/1 n-butanol/toluene. The combined organic layers are dried over sodium sulfate and concentrated. SCX ion-exchange chromatography of the concentrate afforded 70 mg (81%) of the title compound. Electrospray MS M+1 ion=172. 1H-NMR (methanol-d4, 200 MHz): 7.06 (d, 1H, J=8.3 Hz), 6.79 (d, 1H, J=2.4 Hz), 6.65 (dd, 1H, J=2.4 and 8.3 Hz), 2.82 (m, 4H).

Workup

  1. extractionExtract the aqueous layer with 3/1 n-butanol/toluene
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d0b25a4e554e453bb357aa8b5bf90cb4
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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