Formaldehyde → 1,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

HRID 2369337Notes

Reaction equation

HRID 2369337 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH2:16]=O>>[CH2:16]1[C:5]2[NH:6][C:7]3[C:12]([C:4]=2[CH2:3][CH:2]([C:13]([OH:15])=[O:14])[NH:1]1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 6305L-Tryptophan

Product 1

HCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

Procedure

To a mixture of 0.1 NH2SO4 (150 mL) and 37% formaldehyde (80 mL) was added portionwise L-tryptophane (50 g, 245 mmol) with stirring. After being stirred for 4 h at room temperature, the white solid separated out was collected by filtration. The solid cake was washed with water and dried to give 1,2,3,4-tetrahydro-pyrido[3,4-b]indole-3-carboxylic acid, 41 g, (78%); mp 275-276° C. (lit.18 mp 280-282° C.). 1H NMR (DMSO-d6) δ 2.84 (1H, m, CH2), 3.16 (1H, m, CH2), 3.66 (1H, m, CH2), 4.23 (1H, m, CH2), 4.38 (1H, m, CH), 6.98-7.02 (1H, m, ArH), 7.13-7.16 (1H, m, ArH), 7.32-7.34 (1H, m, ArH), 7.45-7.48 (1H, m, ArH), 11.03 (1H, brs, exchangeable, NH).

Workup

  1. stirringAfter being stirred for 4 h at room temperature
  2. customthe white solid separated out
  3. filtrationwas collected by filtration
  4. washThe solid cake was washed with water
  5. customdried

Sources & evidence

ORD record
ord-f31a8e07c06942959be25c6c93660fd9
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

Loading…