Formaldehyde → (3,4-dihydro-2(1H)-isoquinolinylmethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione

HRID 268240

Reaction equation

HRID 268240 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[CH2:11]=O.[CH:13]1[CH:14]=[C:15]2[C:20]3=[C:21]([C:23]([NH:25][C:26](=[O:27])[C:19]3=[CH:18][CH:17]=[CH:16]2)=[O:24])[CH:22]=1>CN(C)C=O>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][N:25]1[C:26](=[O:27])[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:20]=2[C:21](=[CH:22][CH:13]=[CH:14]3)[C:23]1=[O:24]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 70461,2,3,4-TetrahydroisoquinolineHCID 66491Naphthalimide

Product 1

HCID 21551797(3,4-dihydro-2(1H)-isoquinolinylmethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An equimolar mixture of 1,2,3,4-tetrahydroisoquinoline, aqueous formaldehyde, and 1,8-naphthalimide is suspended in a small amount of dimethylformamide and the mixture is heated until dissolution is complete. The solution is allowed to stand at room temperature and the resulting precipitate is filtered off and dried to yield 2-[(3,4-dihydro-2(1H)-isoquinolinylmethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione.

Workup

  1. temperaturethe mixture is heated until dissolution
  2. customto stand at room temperature
  3. filtrationthe resulting precipitate is filtered off
  4. customdried

Sources & evidence

ORD record
ord-86ae842f9f6b4d99be980a88a6d2904a
Source dataset
uspto-grants-1976_03
Patent number
US03947452

Linked notes

Loading…