Fumaric Acid → HCID 131711122, compound

HRID 839603Notes

Reaction equation

HRID 839603 reaction equation
Cl.Cl.[CH3:3][N:4]1[C:8]([NH:9][CH2:10][CH:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:22])=[C:18]([OH:21])[CH:19]=3)[CH2:14][CH2:13][NH:12]2)=[N:7][N:6]=[N:5]1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].C(=O)(O)[O-].[Na+]>O>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[CH3:3][N:4]1[C:8]([NH:9][CH2:10][CH:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:22])=[C:18]([OH:21])[CH:19]=3)[CH2:14][CH2:13][NH:12]2)=[N:7][N:6]=[N:5]1.[CH3:3][N:4]1[C:8]([NH:9][CH2:10][CH:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:22])=[C:18]([OH:21])[CH:19]=3)[CH2:14][CH2:13][NH:12]2)=[N:7][N:6]=[N:5]1

Participants

5

Reactant 3

HCID 444972Fumaric AcidHCID 516892Sodium BicarbonateHCID 20323725HCID 20323725, compound

Product 1

HCID 131711122HCID 131711122, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(1-methyl-1H-tetrazol-5-yl)aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (52.3 g) and water (300 ml) was stirred for 15 minutes at 100° C to give homogeneous solution. Fumaric acid (11.3 g) was added thereto at 100° C, to which was added water (50 ml). The mixture was stirred for 15 minutes, to which were added sodium bicarbonate (25.2 g) over 12 minutes and water (50 ml). The resultant mixture was stirred for 20 minutes at 100° C and the reaction mixture was filtered. The filtrate was allowed to stand at ambient temperature to precipitate crystals. The crystals were collected by filtration, washed with water and dried under reduced pressure to give 1-(1-methyl-1H-tetrazol-5-yl)aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hemifumarate (42.05 g), mp 204° to 207° C (dec.).

Workup

  1. customto give homogeneous solution
  2. stirringThe mixture was stirred for 15 minutes, to which
  3. filtrationthe reaction mixture was filtered
  4. customto stand at ambient temperature
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-78b381ffe3b14d8f828545e3e827b9e8
Source dataset
uspto-grants-1978_06
Patent number
US04096263

Reaction notes

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