Sodium Hydroxide → 8-bromo-2,3,4,5-tetrahydro-1H-benzofuro[3,2-c]azepin-1-one

HRID 2179358Notes

Reaction equation

HRID 2179358 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[C:12](=[N:13]O)[CH2:11][CH2:10][CH2:9][C:7]=3[O:8][C:4]=2[CH:3]=1.[OH-:17].[Na+]>O>[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[C:12](=[O:17])[NH:13][CH2:11][CH2:10][CH2:9][C:7]=3[O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866679977-bromo-3,4-dihydrodibenzo[b,d]furan-1(2H)-one oxime

Product 1

HCID 681084598-bromo-2,3,4,5-tetrahydro-1H-benzofuro[3,2-c]azepin-1-oneYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of the product of step B (1.05 g, 3.74 mmol) and polyphosphoric acid (15 g) was heated to 110° C. for 5 h. After cooling to ambient temperature, the reaction mixture was diluted with water, basified with 10 N NaOH and filtered. The solid obtained was washed with water and dried in vacuo at 70° C. to give 8-bromo-2,3,4,5-tetrahydro-1H-benzofuro[3,2-c]azepin-1-one (858 mg, 82%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ 8.06-7.95 (m, 2H), 7.86 (d, J=1.8 Hz, 1H), 7.45 (dd, J=8.4, 1.8 Hz, 1H), 3.28-3.20 (m, 2H), 3.15 (t, J=6.6 Hz, 2H), 2.07-1.93 (m, 2H).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationfiltered
  3. customThe solid obtained
  4. washwas washed with water
  5. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-8d8a375513934a98810910b8e3d7491a
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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