Hydrogen Bromide → N-(4-Oxo-1,2,3,4-tetrahydronaphthalen-1-yl)formamide

HRID 1155641Notes

Reaction equation

HRID 1155641 reaction equation
[CH:1]1([NH:11][CH:12]=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.Br.[O:15]=O.[Cl-].[Na+]>C(O)(=O)C.O.C(C(C)=O)C(C)C>[O:15]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]([NH:11][CH:12]=[O:13])[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 977OxygenHCID 5234Sodium ChlorideHCID 4165105N-(1,2,3,4-Tetrahydro-1-naphthyl)-formamide

Product 1

HCID 20537306N-(4-Oxo-1,2,3,4-tetrahydronaphthalen-1-yl)formamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
76 °C

Procedure

A mixture of N-(1,2,3,4-tetrahydro-1-naphthyl)-formamide (2.0 g), cobaltous acetate tetrahydrate (0.95 g), a 30% solution of hydrobromic acid in acetic acid (0.925 g) and a 1:1 mixture of acetic acid: methyl isobutyl ketone (40 ml) is stirred and oxygen introduced via a capillary gas delivery tube. The blue reaction mixture is gradually heated to 76° C. in 42 minutes during which time the color changes to purple. The reaction mixture is then allowed to cool to room temperature. Water (40 ml) is added and the mixture saturated with sodium chloride. The mixture is extracted with chloroform (3×20 ml), the combined extracts are washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo. The residual red oil is triturated with ether and after cooling the title compound (0.4 g) collected. Further work-up of the mother liquor affords an additional 0.6 g of title compound.

Workup

  1. customThe blue reaction mixture
  2. temperatureto cool to room temperature
  3. extractionThe mixture is extracted with chloroform (3×20 ml)
  4. washthe combined extracts are washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness in vacuo
  7. customThe residual red oil is triturated with ether
  8. temperatureafter cooling the title compound (0.4 g)
  9. customcollected

Sources & evidence

ORD record
ord-2b556b86f4624d64a47eeef9c6092e15
Source dataset
uspto-grants-1982_06
Patent number
US04332724

Reaction notes

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