Ammonia → HCID 14181389, compound

HRID 2231826Notes

Reaction equation

HRID 2231826 reaction equation
[Cl:1][C:2]1[C:3]2[C:4]3(OCC[O:15]3)[C:5]3[N:6]([CH2:11][CH2:12][CH2:13][N:14]=3)[C:7]=2[CH:8]=[CH:9][CH:10]=1.S(=O)(=O)(O)O.N>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]2[C:4](=[O:15])[C:5]3[N:6]([CH2:11][CH2:12][CH2:13][N:14]=3)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 21284812HCID 21284812, compound

Product 1

HCID 14181389HCID 14181389, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9'-Chloro-2',3',4',10'-tetrahydrospiro[1,3-dioxolane-2,10'-pyrimido(1,2-a)indole] (6.58 g) was added to cooled 98% sulphuric acid (35 ml) with stirring until complete solution was achieved (approx. 2 hours). The solution was poured on to ice (400 ml) and basified to pH9 with conc. ammonia solution. The resulting suspension of the product 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 (4.83 g) which was crystallised from benzene to give 9-chloro-3,4-dihydropyrimido[1,2-a]indol-10(2H)-one as dark orange prisms (3.16 g) darkening above 165° and melting at 170° with decomposition.

Workup

  1. custom(approx. 2 hours)
  2. additionThe resulting suspension of the product
  3. customafter separation
  4. extractionthe aqueous phase was exhaustively extracted with further chloroform
  5. customEvaporation of the
  6. dry with materialdried (MgSO4)
  7. waitextracts left a brownish orange solid (4.83 g) which
  8. customwas crystallised from benzene

Sources & evidence

ORD record
ord-2f928c62e313472b8d2017c27b685798
Source dataset
uspto-grants-1988_11
Patent number
US04784996

Reaction notes

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