Acetic Acid → HCID 23326468, compound

HRID 1380321Notes

Reaction equation

HRID 1380321 reaction equation
[C:1]([BH3-])#N.[Na+].[NH:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=3)=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.C=O.C(O)(=O)C>CO>[CH3:1][N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]([CH3:22])[NH:17][C:18](=[O:21])[NH:19][N:20]=3)=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23326481HCID 23326481, compound

Product 1

HCID 23326468HCID 23326468, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (0.19 g) was added portionwise to a suspension of 6-(1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.74 g), 36% aqueous formaldehyde (0.34 ml), acetic acid (1 ml) and methanol (3 ml) at room temperature. After stirring for 0.5 hours at the same temperature, the resultant precipitates were collected by filtration, washed with methanol, dried, and recrystallized from 70% aqueous ethanol to give 0.66 g of 6-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one.

Workup

  1. customthe resultant precipitates
  2. filtrationwere collected by filtration
  3. washwashed with methanol
  4. customdried
  5. customrecrystallized from 70% aqueous ethanol

Sources & evidence

ORD record
ord-89f839a1b1bc4590836f5ff55a6493ec
Source dataset
uspto-grants-1986_04
Patent number
US04581356

Reaction notes

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