Potassium Hydroxide → [9-(2,5-dichlorobenzyl)-9H-beta-carbolin-3-yl]methylamine

HRID 992577Notes

Reaction equation

HRID 992577 reaction equation
C([NH:3][CH2:4][C:5]1[N:6]=[CH:7][C:8]2[N:9]([CH2:18][C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=3[Cl:26])[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)=O.[OH-].[K+]>C(O)C.O>[Cl:26][C:20]1[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[CH2:18][N:9]1[C:8]2[CH:7]=[N:6][C:5]([CH2:4][NH2:3])=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18412227N-formyl-[9-(2,5-dichlorobenzyl)-9H-beta-carbolin-3-yl]methylamine

Product 1

HCID 9798774[9-(2,5-dichlorobenzyl)-9H-beta-carbolin-3-yl]methylamine

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

This formamide (2.90 g, 7.5 mmol) was treated with potassium hydroxide (5.40 g, 9.4 mmol) in ethanol/water (5:1, 48 mL) at reflux for 6 hours. The resulting suspension was cooled to room temperature, concentrated, and diluted with CH2Cl2 (50 mL). The organic phase was washed with water (2×25 mL), dried (Na2SO4), filtered and concentrated to give [9-(2,5-dichlorobenzyl)-9H-β-carbolin-3-yl]methylamine as a yellow solid. The crude material was recrystallized from ethyl acetate/hexane to give 1.48 grams (55%) of a pale-yellow solid. 1H NMR (CDCl3) δ8.70 (s, 1H), 8.18 (d,J=7.9 Hz, 1H), 8.03 (s, 1H), 7.58 (td,J=7.2, 1.1 Hz, 1H) 7.32-7.42 (6-line m, 3H), 7.20 (dd, J=9.6, 2.6 Hz, 1H), 6.55 (d, J=2.6 Hz, 1H), 5.60 (s, 2H), 4.28 (d, 1H), 1.96 (br s, 2H); MS monoisotopic mass (calculated) 355.1, MH+ (observed) 356.7.

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationconcentrated
  3. additiondiluted with CH2Cl2 (50 mL)
  4. washThe organic phase was washed with water (2×25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-98ca8416d5bf47ffa8870a60b8b22044
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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