Ammonia → HCID 14181388, compound

HRID 2231824Notes

Reaction equation

HRID 2231824 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3(OCC[O:15]3)[C:7]3[N:8]([CH2:11][CH2:12][CH2:13][N:14]=3)[C:9]=2[CH:10]=1.S(=O)(=O)(O)O.N>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[N:8]([CH2:11][CH2:12][CH2:13][N:14]=3)[C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 14181387HCID 14181387, compound

Product 1

HCID 14181388HCID 14181388, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7'-Chloro-2',3',4',10'-tetrahydrospiro[1,3-dioxolane-2,10'-pyrimido(1,2-a)indole] (5.71 g) was added to cooled 98% sulphuric acid (30 ml) with stirring. The solution was then poured on to ice (300 ml) and basified to pH9 with conc. ammonia solution. The resulting suspension was stirred with chloroform (100 ml) and, after separation, the aqueous phase was exhaustively extracted with further chloroform. Evaporation of the combined, dried (MgSO4) extracts left a brownish orange solid which was crystallised from benzene-cyclohexane, giving 7-chloro-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one as orange crystals (3.06 g), darkening above 160° and melting from 168°-170° with decomposition.

Workup

  1. customafter separation
  2. extractionthe aqueous phase was exhaustively extracted with further chloroform
  3. customEvaporation of the
  4. dry with materialdried (MgSO4)
  5. waitextracts left a brownish orange solid which
  6. customwas crystallised from benzene-cyclohexane

Sources & evidence

ORD record
ord-4c8ac307b219439e9e5f9fbf19b6f15a
Source dataset
uspto-grants-1988_11
Patent number
US04784996

Reaction notes

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