Ammonium Chloride → HCID 89906742, compound

HRID 1506848Notes

Reaction equation

HRID 1506848 reaction equation
CO[C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)=[CH:6][C:5]=1[OH:15].[CH:17]1([Mg]Cl)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[NH4+].[Cl-]>C1COCC1>[CH:17]1([C:3]([CH:4]2[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)([OH:16])[C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH:11]=[CH:12][CH:13]=[CH:14]3)=[CH:6][C:5]=2[OH:15])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2764423Methyl 2-hydroxy-4-(1H-pyrrol-1-yl)benzoateHCID 178478990HCID 178478990, compound

Product 1

HCID 89906742HCID 89906742, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 217 mg of 2-Hydroxy-4-pyrrol-1-yl-benzoic acid methyl ester in 4 ml of THF, 2 ml of a solution of cyclohexylmagnesium chloride in THF (2 M) was added slowly at room temperature. The reaction mixture was then heated to reflux for 4 h. After cooling to room temperature it was hydrolized with ice. Saturated aqueous NH4Cl was added until the white precipitate was dissolved. The aqueous phase was extracted with ether. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was used in the next reaction step. Yield: 504 mg.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 4 h
  3. dissolutionwas dissolved
  4. extractionThe aqueous phase was extracted with ether
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was used in the next reaction step

Sources & evidence

ORD record
ord-f4fe837f26e3485a84b817d8443ee9a2
Source dataset
uspto-grants-2015_12
Patent number
US09221784B2

Reaction notes

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