HCID 86587244, compound → HCID 178518722, compound

HRID 1767673Notes

Reaction equation

HRID 1767673 reaction equation
C[O:2][C:3]1[NH:4][C:5](=[O:17])[C:6]2[C:15]([CH:16]=1)=[N:14][CH:13]=[C:12]1[C:7]=2[CH:8]=[CH:9][CH:10]=[CH:11]1>Br>[OH:2][C:3]1[NH:4][C:5](=[O:17])[C:6]2[C:15]([CH:16]=1)=[N:14][CH:13]=[C:12]1[C:7]=2[CH:8]=[CH:9][CH:10]=[CH:11]1

Participants

3

Reactant 1

HCID 86587244HCID 86587244, compound

Product 1

HCID 178518722HCID 178518722, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
100 °C

Procedure

The methyl ether 4c (500 mg, 2.2 mmol) was dissolved in 10 mL HBr (48% in HOAc) in a sealed tube. The reaction was heated to 100° C. for 10 h. After cooling, the reaction was filtered and washed with acetic acid (3×10 mL) and dried in vacuo. The dry weight of the hydrobromide salt 4d was 421 mg, (90%). 1H NMR (d6-DMSO) δ 11.61 (bs, 1H), 10.50 (bs, 1H), 8.62 (d, 1H), 8.30 (d, 1H), 7.89 (t, 1H), 7.71 (t, 1H), 7.65 (d, 1H), 6.81 (d, 1H). Anal Calcd. For C12H9BrN2O2: C, 49.17; H, 3.09; N, 9.56. Found: C, 48.75; H, 3.15; N, 9.36.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction was filtered
  3. washwashed with acetic acid (3×10 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-aea82535138845e7b56cd576bb802e11
Source dataset
uspto-grants-2007_06
Patent number
US07235557B2

Reaction notes

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