Chloride → HCID 837248, compound

HRID 2212612Notes

Reaction equation

HRID 2212612 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[OH-:10].[Na+].[Cl-]>ClCCl>[OH:8][C:6]1[CH:7]=[C:2]([NH:1][C:4](=[O:10])[CH:5]([CH3:9])[CH3:6])[CH:3]=[CH:4][C:5]=1[CH3:9]

Participants

5

Reactant 3

HCID 312ChlorideHCID 14798Sodium HydroxideHCID 178185-Amino-2-methylphenol

Product 1

HCID 837248HCID 837248, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 5-amino-2-methylphenol (30 g, 244 mmol), 10% NaOH (210 mL) and dichloromethane (120 mL) was added at 0° C. slowly isobuyryl chloride (25.5 mL, 244 mmol) in dichloromethane (50 mL). The mixture was stirred at room temperature overnight. The aqueous layer was separated and extracted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure to give 37.2 g of N-(3-hydroxy-4-methyl-phenyl)-isobutyramide (78%). 1H NMR (300 MHz, CDCl3 ppm): δ: 1.21 (d, J=7.03 Hz, 6 H), 2.17(s, 3 H), 2.53 (m, 1 H), 2.58 (s, 3 H), 6.81(dd, J=2.05 Hz, 7.91 Hz, 1H), 6.97 (d, J=7.91 Hz, 1H), 7.38 (d, J=2.05 Hz, 1 H), 8.14 (bs, 1 H), 8.58 (s, 1 H).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-53a1c4a8a7bf400da1e73410de55e299
Source dataset
uspto-grants-2006_09
Patent number
US07102000B2

Reaction notes

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