Hydrochloric Acid → N-cyclopropyl-3-(7-methoxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

HRID 506962Notes

Reaction equation

HRID 506962 reaction equation
[CH:1]1([NH:4][C:5](=[O:27])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[C:22](=O)[CH2:21][C:20]4[C:15](=[CH:16][C:17]([O:24][CH3:25])=[CH:18][CH:19]=4)[C:14]3=[O:26])[CH:7]=2)[CH2:3][CH2:2]1.[BH4-].[Na+].Cl>CO.C(Cl)Cl>[CH:1]1([NH:4][C:5](=[O:27])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:24][CH3:25])=[CH:18][CH:19]=4)[C:14]3=[O:26])[CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67018591N-cyclopropyl-3-(7-methoxy-1,3-dioxo-3,4-dihydro-1H-isoquinolin-2-yl)-4-methylbenzamide

Product 1

HCID 11530361N-cyclopropyl-3-(7-methoxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamideYield 88.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-cyclopropyl-3-(7-methoxy-1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-4-methylbenzamide (1 g) in Methanol (20 ml) and methylene chloride (45 ml) under an atmosphere of argon was added NaBH4 (114 mg) portionwise and the reaction stirred at room temperature for 17 hours. Concentrated hydrochloric acid (0.2 ml) was added and the reaction stirred for a further 4 hours. The reaction mixture was concentrated and the resultant solid triturated with ethyl acetate and air dried to yield N-cyclopropyl-3-(7-methoxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide as a white solid (849 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.10 (s, 3H), 2.86 (m, 1H), 3.39 (s, 3H), 6.72 (d, 1H), 7.21 (d, 1H), 7.41 (d, 1H), 7.50 (d, 1H), 7.67 (s, 1H), 7.71 (d, 1H), 7.89 (d, 1H), 8.44 (d, 1H); Mass Spectrum: M+H+ 349.

Workup

  1. stirringthe reaction stirred for a further 4 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe resultant solid triturated with ethyl acetate and air
  4. customdried

Sources & evidence

ORD record
ord-5de8382142c846528d3a0ab560e2a74c
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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