Methanol → 61636-46-2

HRID 1725560Notes

Reaction equation

HRID 1725560 reaction equation
[C:1]([Cl:4])(=[O:3])C.CO.[OH:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]#[N:11]>C1(C)C=CC=CC=1>[ClH:4].[CH3:1][O:3][C:10](=[NH:11])[C:9]1[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=1[OH:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chloride2×HCID 119072-Hydroxybenzonitrile

Product 1

HCID 13607255761636-46-2Yield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetyl chloride (6.0 g, 76.4 mmol) was added drop-wise to methanol (10 mL) over 30 min. The temperature was kept at 20° C. by cooling the mixture in a water bath. After the addition of acetyl chloride, the solution was stirred for 2 h at room temperature. o-Hydroxybenzonitrile (4.0 g, 33.61 mmol) was added followed by toluene (20 mL). The mixture was stirred at room temperature under an argon atmosphere for 4 days. The precipitate was filtered and washed with toluene. After drying under high vacuum, 2-hydroxy-benzimidic acid methyl ester hydrochloride (2.2 g, 35%) was isolated as a white solid.

Workup

  1. customwas kept at 20° C.
  2. temperatureby cooling the mixture in a water bath
  3. stirringThe mixture was stirred at room temperature under an argon atmosphere for 4 days
  4. filtrationThe precipitate was filtered
  5. washwashed with toluene
  6. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-db03c36d0b6246949dbcf50698db2d00
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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