Sulfuric Acid → Propyl 9-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carboxylate

HRID 992562Notes

Reaction equation

HRID 992562 reaction equation
ClC1C=CC(Cl)=CC=1CN1C2C=NC(C(OC)=O)=CC=2C2C1=CC=CC=2.S(=O)(=O)(O)O.[Cl:32][C:33]1[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][C:34]=1[CH2:35][N:36]1[C:48]2[CH:47]=[N:46][C:45]([C:49]([O:51][CH2:52][CH2:53][CH2:54]C)=[O:50])=[CH:44][C:43]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2>C(O)CC>[Cl:32][C:33]1[CH:59]=[CH:58][C:57]([Cl:60])=[CH:56][C:34]=1[CH2:35][N:36]1[C:48]2[CH:47]=[N:46][C:45]([C:49]([O:51][CH2:52][CH2:53][CH3:54])=[O:50])=[CH:44][C:43]=2[C:42]2[C:37]1=[CH:38][CH:39]=[CH:40][CH:41]=2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 9908122methyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylateHCID 9910378butyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

Product 1

HCID 18412200Propyl 9-(2,5-Dichlorobenzyl)-9H-beta-carboline-3-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

Methyl 9-(2,5-dichlorobenzyl)-9H-β-carboline-3-carboxylate (195 mg, 0.5 mmol) was refluxed with n-propanol (15 mL) and concetrated sulfuric acid (1.5 mL) as described for the synthesis of the butyl 9-(2,5-dichlorobenzyl)-9H-β-carboline-3-carboxylate, affording an ivory-colored solid (152 mg, 74%). 1H NMR (CDCl3) δ8.94 (s, 1H), 8.85 (s, 1H), 8.28 (d, J=8.3 Hz, 1H), 7.64 (t, J=7.5 Hz, 1H), 7.45-7.40 (m, 3H), 7.22 (dd, J=8.5, 2.3 Hz, 1H), 6.55 (s, 1H), 5.66 (s, 2H), 4.45 (t,J=7 Hz, 2H), 1.93 (m, 2H), 1.07 (t, J=7 HZ, 3H); MS (APCI; (M+H)+) m/z 413.

Sources & evidence

ORD record
ord-a926c52081f948d38b942db6993915a7
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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