Hydrochloric Acid → HCID 23460506, compound

HRID 1414573Notes

Reaction equation

HRID 1414573 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[O:5][C:6]1[CH:7]=[CH:8][C:9]([N+:18]([O-])=O)=[CH:10][C:11]=1[C:12]2=[O:17].[ClH:21]>>[ClH:21].[NH2:18][C:9]1[CH:8]=[CH:7][C:6]2[O:5][C:4]3[C:13](=[CH:14][CH:15]=[CH:16][C:3]=3[O:2][CH3:1])[C:12](=[O:17])[C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 23460505HCID 23460505, compound

Product 1

HCID 23460506HCID 23460506, compound

Procedure

5-Methoxy-2-nitroxanthone (5.0 g.) is added in small portions during 30 minutes to a stirred mixture of stannous chloride dihydrate (30 g.) and concentrated hydrochloric acid (30 ml.) heated on a steam-bath. The mixture is stirred and heated on a steam-bath for a further 2 hours. The precipitate is filtered off, washed with water and stirred with 5N sodium hydroxide solution (50 ml.) for 1 hour. The solid is filtered off, made into a slurry with methanol and treated with ethereal hydrochloric acid. The solid is crystallised from methanol-ether to give 2-amino-5-methoxyxanthone hydrochloride, m.p. 271°-273° C.

Workup

  1. temperatureheated on a steam-bath
  2. temperatureheated on a steam-bath for a further 2 hours
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. stirringstirred with 5N sodium hydroxide solution (50 ml.) for 1 hour
  6. filtrationThe solid is filtered off
  7. additiontreated with ethereal hydrochloric acid
  8. customThe solid is crystallised from methanol-ether

Sources & evidence

ORD record
ord-618ed46d7c074f5f910596788658515e
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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