Sulfuric Acid → HCID 131710894, compound

HRID 2420283Notes

Reaction equation

HRID 2420283 reaction equation
[CH:1]([NH:4][C@H:5]1[C@H:10]([OH:11])[C:9]([CH3:13])([CH3:12])[O:8][C:7]2[CH:14]=[CH:15][C:16]([N+:18]([O-])=O)=[CH:17][C:6]1=2)([CH3:3])[CH3:2].C(OCC)C.[S:26](=O)(=[O:29])([OH:28])[OH:27]>C(O)C.Cl>[S:26]([O:11][C@@H:10]1[C:9]([CH3:13])([CH3:12])[O:8][C:7]2[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:6]=2[C@H:5]1[NH:4][CH:1]([CH3:3])[CH3:2])([OH:29])(=[O:28])=[O:27]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 13222931HCID 13222931, compound

Product 1

HCID 131710894HCID 131710894, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Trans-4-Isopropylamino-3,4-dihydro-2,2-dimethyl-6-nitro-2H-benzo[b]pyran-3-ol (3.54 g.) was added to a solution of stannous chloride (7.90 g.) in ethanol (36 ml.) and concentrated hydrochloric acid (60 ml.) and stirred for 3 hours at ambient temperature. After dilution, work-up via diethyl ether gave a gum (3.25 g.). Purification of this gum (2.00 g.) by application to silica gel plates and development with ethyl acetate/60°-80° petroleum ether mixture gave an amorphous solid (1.01 g.) which was dissolved in dilute sulphuric acid and evaporated to dryness to yield trans-4-isopropylamino-3,4-dihydro-2,2-dimethyl-6-amino-2H-benzo[b]pyran-3-ol sulphate as a light brown solid m.p. 180° - 190°.

Workup

  1. customPurification of this gum (2.00 g.) by application to silica gel plates and development with ethyl acetate/60°-80° petroleum ether mixture
  2. customgave an amorphous solid (1.01 g.) which
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-21d5b263398b4bff939d6f84d5de27f6
Source dataset
uspto-grants-1978_08
Patent number
US04110347

Reaction notes

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