Acetone → HCID 135574109, compound

HRID 1954050Notes

Reaction equation

HRID 1954050 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13]C)[C:9]([CH3:15])=[N:8][C:7]([C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[C:18]([O:24]C)[CH:17]=1)=[CH:6]2.C(=O)=O.CC(C)=O.B(Br)(Br)Br>C(Cl)(Cl)Cl.ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[C:9]([CH3:15])=[N:8][C:7]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:24])[CH:17]=1)=[CH:6]2

Participants

7

Reactant 4

HCID 180AcetoneHCID 280Carbon DioxideHCID 25134Boron tribromideHCID 7674186,7-Dimethoxy-1-methyl-3-(3,4-dimethoxyphenyl)isoquinoline

Product 1

HCID 135574109HCID 135574109, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-50 °C

Procedure

Compound 12a (250 mg, 0.74 mmol) was dissolved in 5 mL dry chloroform and chilled to -50° C. using a mixture of dry ice and acetone. To this mixture was added dropwise 7.4 mL of a 1.0 M solution of boron tribromide in dichloromethane. The reaction mixture was allowed to come to room temperature over a period of 4 h. The precipitate was filtered and washed twice with 2 mL portions of ether. This crude product was recrystallized from ethanol to give 13 in 98% yield as white needles; mp >280° C. dec; IR (Nujol) 3326, 1602, 1531; 1H NMR (CD3OD) δ 3.08 (s, 3H), 6.98 (d, 1H, J=8.1), 7.19 (dd, 1H, J=8.1, 1.9), 7.24 (s, 1H), 7.37 (s, 1H), 7.61 (s, 1H), 7.94 (s, 1H); 13C NMR (CD3OD) δ 17.8, 109.6, 110.6, 116.1, 117.3, 119.6, 121.2, 122.8, 125.6, 138.4, 142.5, 147.7, 149.5, 152.0, 154.3, 158.3; HRMS calcd for C16H13NO4 : 283.0844; found 283.0839.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed twice with 2 mL portions of ether
  3. customThis crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-b6470e60e2e94e22836bcc78ee38642b
Source dataset
uspto-grants-2000_09
Patent number
US06121275

Reaction notes

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