Ammonia → 5-Bromotryptamine

HRID 1263264

Reaction equation

HRID 1263264 reaction equation
[Br:1][C:2]1[CH:13]=[C:12]2[C:5]([NH:6][C:7](C(O)=O)=[C:8]2[CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.N>>[Br:1][C:2]1[CH:13]=[C:12]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 7627893-(2-Amino-ethyl)-5-bromo-1H-indole-2-carboxylic acid

Product 1

HCID 771585-BromotryptamineYield 58%

Procedure

A mixture of 1.00 g. (3.53 mmoles) of 5-bromo-tryptamine-2-carboxylic acid and 80 ml. of 10% aqueous sulfuric acid is stirred and refluxed for 30 hours. The pH of the mixture is adjusted to 9 with concentrated aqueous ammonia under cooling in an ice bath, and the alkaline mixture is extracted with 4×20 ml. of chloroform. The organic extracts are combined, washed with 5% aqueous sodium hydroxide solution and then with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate is evaporated in vacuo. 0.48 g. (58%) of 5-bromo-tryptamine are obtained as an oily residue.

Workup

  1. additionA mixture of 1.00 g
  2. temperaturerefluxed for 30 hours
  3. temperatureunder cooling in an ice bath
  4. extractionthe alkaline mixture is extracted with 4×20 ml
  5. washwashed with 5% aqueous sodium hydroxide solution
  6. dry with materialwith water, dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-99bad48d7830441ab623d24442d4e9e0
Source dataset
uspto-grants-1984_06
Patent number
US04456607

Linked notes

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