Butyl bromide → HCID 131715243, compound

HRID 2308949Notes

Reaction equation

HRID 2308949 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[CH:9]([CH2:10][C:11](=[O:15])[NH:12][N:13]=3)[CH2:8][CH2:7][C:6]=2[CH:16]=1.[CH2:17](Br)[CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:17]([N:13]1[CH:14]2[CH:9]([CH2:8][CH2:7][C:6]3[CH:16]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=32)[CH2:10][C:11](=[O:15])[NH:12]1)[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 13603301103603-13-0

Product 1

HCID 131715243HCID 131715243, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of dl-8-amino-4,4a,5,6-tetrahydro-2H-benzo(h)-cinnolin-3-one (3 g) and n-butyl-bromide (5.7 g) in acetone (75 ml) is heated at reflux temperature in the presence of fine powdered potassium carbonate (5 g). The mixture is filtered, the acetone is evaporated and the residue is partitioned between water and ethyl acetate. The usual work-up affords a crude compound (3.9 g) which is crystallized from methanol to yield dl-1-n-butyl-8-amino-4,4a,5,6-tetrahydro-2H-benzo(h)-cinnolin-3-one m.p. 141°-142° C.

Workup

  1. filtrationThe mixture is filtered
  2. customthe acetone is evaporated
  3. customthe residue is partitioned between water and ethyl acetate
  4. customThe usual work-up affords a crude compound (3.9 g) which
  5. customis crystallized from methanol

Sources & evidence

ORD record
ord-8a4797082807483782e1455feeb51dfb
Source dataset
uspto-grants-1987_09
Patent number
US04692447

Reaction notes

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