Hydrochloric Acid → 5-Amino-5,7-dihydro-6H-dibenzo[a,c]cyclohepten-6ol Hydrochloride

HRID 860190

Reaction equation

[CH:1]1[C:6]2[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[CH2:9][C:10](=[O:12])[CH2:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[N:17](OCCCC)=O.[ClH:24]>CCOCC>[ClH:24].[NH2:17][CH:9]1[C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:11][CH:10]1[OH:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A round bottom flask was charged with 5,7-dihydro-6H-dibenzo[a,c]cyclohepten-6-one (1.0 g, 4.81 mmol) (CAS# 1139-82-8, prepared as described in Tetrahedron Letters, Vol. 28, No. 23, (1987), pp 2633–2636) and butyl nitrite (0.673 ml, 5.77 mmol) (Aldrich) in Et2O. The solution was cooled to 0° C. and treated drop-wise with a saturated solution of HCl(g)/Et2O. After 5 h at 0° C. the resulting precipitate was filtered, rinsed with cold Et2O and vacuum dried to give the title compound as a colorless solid.

Workup

customprepared
filtrationAfter 5 h at 0° C. the resulting precipitate was filtered
washrinsed with cold Et2O and vacuum
customdried

Sources & evidence

ORD record: ord-1927786e16704dc49ebeb26f01d69283
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153847B2

Linked notes

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