Boron tribromide → N-Methylsalicylamide

HRID 2086156Notes

Reaction equation

HRID 2086156 reaction equation
[CH:1]1([N:5](C)[C:6](=[O:27])[C:7]2[CH:12]=[C:11](OC3C(C)=CC([N+]([O-])=O)=CC=3C)[CH:10]=[CH:9][C:8]=2[O:25]C)CCC1.B(Br)(Br)Br>C(Cl)Cl>[OH:25][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]([NH:5][CH3:1])=[O:27]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22728151HCID 22728151, compound

Product 1

HCID 74624N-Methylsalicylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-Cyclobutyl-5-(2,6-dimethyl-4-nitro-phenoxy)-2-methoxy-N-methyl-benzamide (1.65 grams, 4.3 mmol) in methylene chloride (35 mL) at room temperature was added slowly boron tribromide (1M in methylene chloride, 8.6 mL, 8.6 mmol). The resulting mixture was stirred at room temperature for 4 hours, and quenched by pouring into ice water (100 mL), stirred for 1 hour at room temperature, then extracted with methylene chloride (3 times 30 mL). The combined organic extracts were washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered, and concentrated to give 2-hydroxy-N-methyl benzamide as a brown solid which was subjected directly to hydrogenation without further purification. 1H NMR (400 MHz, CDCl3) δ9.43 (s, 1H), 8.00 (s, 2H), 6.97-6.93 (d+dd, 2H), 6.42 (d, 1H), 4.44 (m, 1H), 2.96 (s, 3H), 2.22 (s, 6H), 2.19-2.14 (m, 2H), 1.87-1.55 (m, 4H). MS (APCI+) Calc: 370.2, Found: 371.2 (M+1).

Workup

  1. customquenched
  2. additionby pouring into ice water (100 mL)
  3. stirringstirred for 1 hour at room temperature
  4. extractionextracted with methylene chloride (3 times 30 mL)
  5. washThe combined organic extracts were washed with saturated aqueous NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5ed7848997bc44b7a6b99d6ae0002efe
Source dataset
uspto-grants-2004_04
Patent number
US06723744B2

Reaction notes

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