Methanol → HCID 10065450, compound

HRID 1684110Notes

Reaction equation

HRID 1684110 reaction equation
C[O:2][CH2:3][C:4]1[N:5]([CH3:28])[C:6](=[O:27])[C:7]2[C:8]([N:26]=1)=[C:9]([O:24]C)[C:10]1[C:11](=[O:23])[N:12]([CH3:22])[C:13]([CH2:19][O:20]C)=[N:14][C:15]=1[C:16]=2[O:17]C.CO.[K+].[Br-]>C1C=CC=CC=1>[OH:2][CH2:3][C:4]1[N:5]([CH3:28])[C:6](=[O:27])[C:7]2[C:8]([N:26]=1)=[C:9]([OH:24])[C:10]1[C:11](=[O:23])[N:12]([CH3:22])[C:13]([CH2:19][OH:20])=[N:14][C:15]=1[C:16]=2[OH:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 253877Potassium BromideHCID 10249791HCID 10249791, compound

Product 1

HCID 10065450HCID 10065450, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 172 mg 10.441 mmol) of 15, suspended in 50 mL of dry benzene, was added an excess of 99% BBr, (up to 10 fold excess). The resulting mixture was refluxed for 7 hours. After cooling the reaction mixture to room temperature, methanol was added to quench the reaction. The solvent was evaporated off in vacuo and the product purified by rinsing successively with water and methanol and then dried: 106.5 mg (72%) yield; dec pt >245° C. IR (KBr pellet) 3384, 1645, 1618, 1443, 1430, 1379, 1325, 1209, 1079, 965, 793 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) 11.86 (2H, s, 5- and 10-hydroxyls), 4.62 (4H, s, methylenes), 3.61 (6H, s, 3- and 8- methyls); mass spectrum (EI model m/z 334 (P+).

Workup

  1. additionwas added an excess of 99% BBr, (up to 10 fold excess)
  2. temperatureThe resulting mixture was refluxed for 7 hours
  3. customto quench
  4. customthe reaction
  5. customThe solvent was evaporated off in vacuo
  6. customthe product purified
  7. washby rinsing successively with water and methanol
  8. customdried
  9. custom106.5 mg (72%) yield

Sources & evidence

ORD record
ord-f13d875db5bb4c078f19fb0245330623
Source dataset
uspto-grants-1997_06
Patent number
US05639881

Reaction notes

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