Water → (9H-Pyrido[3,4-b]indol-1-yl)methanol

HRID 1733223Notes

Reaction equation

HRID 1733223 reaction equation
[C:1]([C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3)(OC)=[O:2].[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1>[OH:2][CH2:1][C:5]1[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]=[CH:7][N:6]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

5

Reactant 3

HCID 962WaterHCID 5972669H-Pyrido(3,4-b)indole-1-carboxylic acid, methyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 5318284(9H-Pyrido[3,4-b]indol-1-yl)methanolYield 21.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of dry tetrahydrofuran were dissolved 160 mg of 1-carbomethoxy-9H-pyrido[3,4-b]indole. The solution was cooled with ice, 2 ml of diisobutyl-aluminum hydride were added and the reaction mixture allowed to stand for 2 hours. Unreacted reagent was then decomposed with a small amount of water and the mixture extracted with chloroform. The chloroform was removed by distillation and the residue recrystallized from methanol to yield 30 mg of 1-hydroxymethyl-9H-pyrido[3,4-b]indole as pale-yellow needles melting at 228°-230° C. The IR spectrum shows the absorption peak at 1680 cm-1 has disappeared, with an intense absorption being observed at 1630 cm-1. Mol. wt. (based on mass spectrum) 198.

Workup

  1. additionwere added
  2. extractionthe mixture extracted with chloroform
  3. customThe chloroform was removed by distillation
  4. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-7cffc5dff0dd416793c130eddbf9adfa
Source dataset
uspto-grants-1980_12
Patent number
US04241064

Reaction notes

Loading…