Formaldehyde → HCID 21462980, compound

HRID 1940533Notes

Reaction equation

HRID 1940533 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[CH2:11]=O.[NH:13]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[CH:15]=[CH:14]1.[OH-].[Na+]>C(O)(=O)C.O>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][C:15]1[C:16]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[NH:13][CH:14]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 70461,2,3,4-TetrahydroisoquinolineHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 14798Sodium Hydroxide

Product 1

HCID 21462980HCID 21462980, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1,2,3,4-Tetrahydroisoquinoline (1.37 g, 10.0 mmol) was dissolved in acetic acid (4 ml) and water (2 ml). 37% Aqueous formaldehyde (0.9 ml, 12 mmol) was added and the reaction mixture stirred for five minutes, 1H-pyrrolo[2,3-b]pyridine (1.18 g, 9.99 mmol) added and the resulting solution stirred at room temperature for 20 h. The reaction mixture was poured into 2M aqueous sodium hydroxide solution (50 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water (50 ml) and brine (50 ml). The organic phase was dried (MgSO4) and concentrated in vacuo to give a lemon solid. Recrystallisation from toluene gave the title compound (0.935 g, 36%), as an off-white solid, m.p. 190°-192° C.; (Found: C, 77.51; H, 6.50; N, 15.57. C17H17N3 requires C, 77.54; H, 6.51; N, 15.96%); δH (DMSO-d6) 2.68 (2H, t, J 7.8 Hz, CH2), 2.77 (2H, d, J 7.5 Hz, CH2), 3.55 (2H, s, CH2), 3.79 (2H, s, CH2), 6.97-7.07 (5H, m, ArH), 7.41 (1H, d, J 1.8 Hz, ArH), 8.03 (1H, dd, J 7.8, 1.5 Hz, 4-H), 8.20 (1H, dd, J 4.6, 1.5 Hz, 6-H), and 11.48 (1H, br s, NH); m/z (CI+, NH3) 264 (M+1)+.

Workup

  1. stirringthe resulting solution stirred at room temperature for 20 h
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined extracts were washed with water (50 ml) and brine (50 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a lemon solid
  7. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-78203d7d5ada499087cc03dcb3f60f09
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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