Phosphorus oxychloride → 9-chloro-5,6,7,8-tetrahydroacridine-3-carboxylic Acid

HRID 520820Notes

Reaction equation

HRID 520820 reaction equation
O=[C:2]1[C:15]2[CH:14]=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][C:10]=2[NH:9][C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:2]1[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:8]=2[N:9]=[C:10]2[C:15]=1[CH:14]=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 575164539-Oxo-5,6,7,8,9,10-hexahydro-acridine-3-carboxylic acid

Product 1

HCID 43406149-chloro-5,6,7,8-tetrahydroacridine-3-carboxylic AcidYield 88%

Conditions

Temperature
100 °C

Procedure

A suspension of 9-oxo-5,6,7,8,9,10-hexahydro-acridine-3-carboxylic acid (VIa) (10 g, 4.1 mmols) in phosphorous oxychloride (50 mL) was heated to 100° C. for 1 h. Reaction completion was monitored by TLC. After completion, the reaction mixture was cooled to 25° C. and excess phosphorous oxychloride was removed under vacuum. The residue was mixed with ice (50 g) and the pH was adjusted to 4-5 with solid sodium bicarbonate. The solid obtained was filtered, washed with water (250 mL) and dried under vacuum to get 9.6 g (88%) of compound (Vila) as a white solid.

Workup

  1. customReaction completion
  2. temperatureAfter completion, the reaction mixture was cooled to 25° C.
  3. customexcess phosphorous oxychloride was removed under vacuum
  4. additionThe residue was mixed with ice (50 g)
  5. customThe solid obtained
  6. filtrationwas filtered
  7. washwashed with water (250 mL)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-b316de3a29c0460c831b7f6c88c06d6b
Source dataset
uspto-grants-2016_05
Patent number
US09328093B2

Reaction notes

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