HCID 12674740, compound → HCID 13533224, compound

HRID 2398944Notes

Reaction equation

HRID 2398944 reaction equation
Br[CH:2]([CH2:17][CH3:18])[C:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)=[O:4]>C(N)(CC)C>[CH:11]([NH:10][CH:2]([CH2:17][CH3:18])[C:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)=[O:4])([CH2:6][CH3:5])[CH3:12]

Participants

3

Reactant 1

HCID 12674740HCID 12674740, compound

Product 1

HCID 13533224HCID 13533224, compoundYield 170.3%

Reagents, catalysts & solvents 1

HCID 24874Sec-ButylamineSolvent

Conditions

Temperature
60 °C

Procedure

200 ml of sec-butylamine (III) was added to 10 g of 5-(α-bromobutyryl)-8-hydroxycarbostyril (IV) obtained as described in Examples 1 to 3, and the resulting mixture was heated at a temperature of 60° C for 20 hours followed by concentration to dryness. Crystals which formed upon addition of water were filtered, dissolved in 50 ml of ethanol, and the resulting solution was adjusted to a pH of 1 with concentrated hydrochloric acid. The precipitated crystals were filtered and recrystallized from methanol to obtain 8.3 g of 5-(α-sec-butylaminobutyryl)-8-hydroxycarbostyril (II) hydrochloride having a melting point of 212°-214° C (with coloring and decomposition).

Workup

  1. customobtained
  2. concentrationfollowed by concentration to dryness
  3. customCrystals which formed upon addition of water
  4. filtrationwere filtered
  5. dissolutiondissolved in 50 ml of ethanol
  6. filtrationThe precipitated crystals were filtered
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ac726d7681ef480aae52f215de5c4df5
Source dataset
uspto-grants-1977_05
Patent number
US04026897

Reaction notes

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