Methanol → HCID 20463967, compound

HRID 325671Notes

Reaction equation

HRID 325671 reaction equation
B(Br)(Br)Br.C([NH:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([NH2:21])=[C:14]([O:19]C)[CH:15]=2)[CH2:10]1)(=O)C.CO.C(Cl)[Cl:25]>>[ClH:25].[ClH:25].[NH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([NH2:21])=[C:14]([OH:19])[CH:15]=2)[CH2:10]1

Participants

5

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 25134Boron tribromideHCID 20463964HCID 20463964, compound

Product 1

HCID 20463967HCID 20463967, compound

Procedure

2.7 ml of boron tribromide are added to a solution of 23 g of 2-acetamido-7-amino-6-methoxy-1,2,3,4-tetrahydronaphthalene in methylene chloride at -60° C. The mixture is left to return to ambient temperature, cooled to -60° C. and neutralised with methanol. After evaporation to dryness, 12 N hydrochloric acid is added and the mixture is heated under reflux for 48 hours. It is then left to cool and the crystals formed are filtered off, washed with acetone and then with diethyl ether and dried. The product collected melts above 300° C.

Workup

  1. waitThe mixture is left
  2. customto return to ambient temperature
  3. customAfter evaporation to dryness, 12 N hydrochloric acid
  4. additionis added
  5. temperaturethe mixture is heated
  6. temperatureunder reflux for 48 hours
  7. waitIt is then left
  8. temperatureto cool
  9. customthe crystals formed
  10. filtrationare filtered off
  11. washwashed with acetone
  12. dry with materialwith diethyl ether and dried
  13. customThe product collected melts above 300° C.

Sources & evidence

ORD record
ord-76405077d90c407cb82a92a8b5a6e7a2
Source dataset
uspto-grants-1984_04
Patent number
US04442126

Reaction notes

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